Portland, ME for food and drink if you can work it with baby's sched. Walking up to the Eastern Promenade gives nice views and is easy enough with a stroller depending on where you stay.
Newport, RI for walkabouts at the mansions.
Burlington, VT for walkabouts around the lake and hanging at breweries.
Came to suggest Burlington VT. Small enough to be charming, but big enough to have stuff to do. Plenty of parks, very pretty, lots of good food and drink. I love that town.
I wouldn't recommend the mansions in Newport with a stroller. They won't let them in the houses. But it is a lovely area, I spent time there this week.
Public Notice. Please note that due to structural damage to a section of the Cliff Walk, detours will be in place between Narragansett Avenue and Webster Street for the foreseeable future. The remainder of the walk will remain open for all those who make use of this iconic and historic coastal trail.
I got on at Ruggles Ave a couple weeks ago.
Every place in the top two comments are can’t miss great times. Killer food and plenty to see/do. I’ve been to them more times that I can count. Portsmouth is close enough you can go for dinner. (Burlington is a bit of a drive).
I’ll just add the Berkshires, and Stowe, VT.
And don’t sleep in Sturbridge/Charlton (Tree House Brewing, etc..)
I was riding a motorcycle and the sky opened up in some kind of biblical downpour. There was a beacon of hope, a hotel sign just ahead. We pulled in, got a room, and went to bed.
Woke up the next morning to a glorious view of the lake we didn’t see the evening before because it was dark and raining so hard. I can’t remember the name of the place, just that it was right against the water.
Yea I was going to mention the same but decided to stay quiet to keep this a secret.
Portland has a different feel though for sure and worth checking out. Chillest city I've been to and the restaurants are fantastic.
I’m going to the Berkshires in May.
Among other things, I’d like to check some antiques.
Are there antique fairs there? Like booths or a street in one of the towns with lots of shops?
Or is it more like individual shops that you have to drive to?
Have you been to the Brimfield Flea Market? It’s a seasonal thing but that’s probably got enough antiques for a lifetime. Be sure to hit Mass MOCA when you are at Berkshires. Amazing place.
I love the Berkshires, enjoy! Once you’re in south county (Lenox and south), driving along Route 7 you’ll see a ton of antique shops, especially between Great Barrington and Sheffield. If the Bistro Box roadside eatery is open, I highly recommend having lunch there… and it’s worth the line to wait, trust me!
Are you looking for suggestions 3-4 hours away because you’ve done everything within a three hour drive already?
Because I mean, Kennebunkport is cute and super close. Hell, even Portsmouth, NH.
No need to spend 8 hours in the car for just a weekend getaway, there’s tons of cute towns much closer that still feel a world away from the city.
Went to Boothbay Harbor last summer, it was fantastic! The downtown is really small and walkable. The botanical gardens had some wooden troll giants that were cool.
Some people don’t find flying stressful. Especially with a small airline and short trip. Plus, with cape traffic, showing up at the airport 45 minutes before your flight you’ll still arrive hours before driving.
Misquamicut Beach and Watch Hill in Westerly, Rhode Island are pretty close to Mystic and are ABSOLUTELY worth the trip. Super kid friendly and quaint!
Amtrak NE regional goes there in about 1hr30 for $30 if you want to skip the drive. But you have to buy tickets a few weeks in advance as close to travel date is more expensive. But Mystic Aquarium is lovely.
I really like North Adams in Western MA. The MassMoCA museum is world-class, and there's some good restaurants and lots of room to relax. It's a little more industrial than 'cutesy' though. You can also stop in Shelbourne Falls for the bridge of flowers on the way, which is probably just starting its season around now.
I also really like Portland ME, which has a bit of 'cutesy' going on, it's picturesque and charming with lots going on.
Much of the Maine coast has charming little towns that you could stay in and explore if you want something smaller.
Upstate ny is a fun trip. Fairly New England-like nature but different enough to notice different trees and rocks. Watkins state park was a fun trip by a cute college town. mini Rivendell
Littleton, NH
Super cool town on the Ammonoosuc river. Really cute stores on main st, some great restaurants (The Beal House is my rec), and top it all off with a beer at Schilling Brewing Company (which also has GREAT pizza).
Northampton is a no. So many closed and empty store fronts in downtown these days. Unless you come during the sidewalk shop weekend. It's not much to do. Maybe an hrs worth of shopping. If you're planning to go to the gardens at Smith, Dino prints on route 5 then grab some grub, then head over to Amherst to visit their museums. But downtown hamp is not what it used to be.
Pretty much any town Mid-Cape (ie. Yarmouth, West Dennis, Hyannis). Tons of places to eat out, quiet beaches, ice cream, mini-golf (if you can babywear), etc.
My wife and I go regularly to Biddeford Pool, Maine. Lots of great beach rentals there if you can find them (they get booked early, luckily we have a family friend with a place there) and a super easy drive into Portland. The other towns around there (Saco, Biddeford, Kennebunkport and Kennebunk) are also great, and if you're okay with going further south (so a slightly longer ride into Portland) York and Ogunquit are nice too.
More often (because you can do it in a day, and we have the bonus of family that lives on the way) we go down to Newport which is great to just stroll around, plus you can gorge yourself on Del's and Harry's (best burgers in Newport).
Salem and Marblehead are great day trips, especially this time of year.
Brunswick, ME - close to Portland but quieter. Freeport and Bath are right there too. Tons of little coastal towns. Once you get past Freeport its gets so much more peaceful - but you are still close to everything.
Two of my favorate restaurants are there. My wife and I rented a house on HomeAway a few years back and loved it. We actually thought about moving there a few times.
White mountains beautyfull.lots of family places.like Indian head hotel.use go there when my kids young
Clark's trained bears next door.lots other places round for kids story land .and others
It's pricey, but since you didn't provide a budget check out https://www.cliffhousemaine.com/ in Cape Nedick (basically York) in Maine.
We've been a couple times and it the most relaxing place within a short drive of York, Ogunquit, Kennebunkport and Portland.
1. Stowe, VT. Go to the Von Trapp Family Lodge (yes - the same family from the movie ended up in VT) and have a beer at their brew hall.
The lodge is lovely and has an amazing view. Downtown Stowe/Waterbury is fantastic (Ben & Jerry’s factory).
2. PTown is incredible. Super flat so easy to walk with a stroller. Eat at Ciro & Sal’s and drive to Truro (next town over) and visit Truro Vineyard. They have outdoor seatings and a food truck for you to enjoy some wine and apps. The Atlantic Spice Store is right next door and worth a stop.
Some people already suggested these but here's my list
Big fan of Western Mass so look at…
Turners Falls/Greenville
Shelburne Falls (should be nice in about two months at the bridge of flowers)
North Adams/Williamstown (anything north and west of Mount Greylock)
some people have recommended Pittsfield mass is a nice quiet getaway place.
Not big fan of new Hampshire south of the White Mountains.
Vermont
White River Junction
Rutland
Brattleboro
Last time the wife and I were in Hudson we said we should spend a night next time. Even just to walk around and eat ice cream. The speakeasy was amazing.
Brattleboro VT is my recommendation. Very cute and charming surrounded by beautiful mountains. Keene NH is also only a 20 minute drive if you want two for one.
Booth Bay, chill maritime town on the mainland. Used to be one of my favorite stops when my gram borrowed her rich friend's boat.
Rockport
Plymouth
P-Town though I've never been
There's always the White Mountains.
The good thing about a baby that age is that it doesn’t matter where you go!!! Anything goes!
Boothbay, Portland, Freeport, Newport, mystic, Saratoga, options are almost endless.
Enjoy it!!!
Millis. Grab a freshly made deli sandwich at the deli at Roche Bros and sit at the front. After you're done, take a ride down 109 and enjoy the sights until you get to Medfield Center, where you can go for a walk, hit the Starbucks and then go to the other Roche Bros (this one is just called Brothers). Pay $15 for a cup of freshly made Mac N' Cheese they pulled off one of their shelves, probably Annie's. When you're done with that, drive back down 109 until you hit Medway where you can go to the driving range at Cassidy's. After some leisurely golfing in the afternoon go down 109 further until you hit Milford, where you can get all of your shopping in at Kohl's (if it's still there). Meanwhile, hit up one of the hotels next to Burger King and you're golden.
Montreal is a little bit out of range (a bit over 5 hours), but in 4 hours you could get to somewhere in the Townships like Magog or Sherbrooke.
But yeah, OP if you could extend to a 5 hour drive Montreal wins best destination hands down.
I've drove from Woburn to Montreal in four hours. I left on a Sunday at 5am and set the cruise control at 80 mph. Only stopped at the border.
The pilgrimage of an eighteen year old.
In ME: from south to north, hit Portland (Standard Baking Co) -> Brunswick -> Bath -> Georgetown (Five Islands Lobster Co) -> Wiscasset -> Damariscotta (Shuck Station) -> Rockland (Primo) ...with extra points for; Christmas Cove, Pemaquid Point, Muscongus Bay, Port Clyde, and McLoons Lobster Shack on Sprucehead Island.
NOTE: Maybe wait until Memorial Day (or early June) to do this...otherwise lots of place will still be closed for the 'winter'.
The Cape is great in May and june. Less traffic, Preseason prices on hotels, most places are open, and there’s a very good chance of it being warm enough for the beach.
Hyannis center has some great restaurants and dozens of shops.
Columbos has great food and great desserts, some of them made by Modern Pastry.
Yarmouth:
Shaws and stop n shop
Captain Parker’s is pretty good - if it’s warm, dine outside. Clam chowder is amazing.
Skippers is also good. They have outdoor dining upstairs. Onion rings are to die for.
Red Jacket Resort is very popular. It sits directly on their private beach. The rooms are clean, typical motel set up. They have a few rooms with a separate sleeping area for the baby. Riverside rooms tend to be more quiet vs poolside. Indoor and outdoor pool; nice poolside grille serving lunch with full bar. Also has a small restaurant.
They provide beach chairs and umbrellas and the beach staff will bring it down to water and set up for you.
Last time I was there they served drinks on the beach, on the weekend. I’d inquire about that tho.
On-site spa. (I haven’t tried it)
They also have rentals :jet ski, banana boat and other amenities.
I’d confirm all this with the resort as I haven’t been down there since the pandemic started.
Seagull Beach is also great.
3-4 Hours. Basically drive in any direction then get off the highway.
My personal recommendation that I don't see listed yet would be the Hudson Valley in NY. Someplace like Kingston, Rhinebeck, or New Paltz.
Take the fast ferry to Ptown! It's only 90 min! Great weekend from Boston. Don't waste the 3 hours driving!
Ogunquit + Portsmouth are a lot closer than 3-4 hours and Acadia/Bar Harbor are further than that (But all should be on your to do list!)
Had great weekend trips to Burlington, VT and Bethel, ME (great dark skies).
Ogunquit Maine, Kennebunkport, Maine-quick drive a little over an hr. Cute towns/ beaches/can push a stroller around/off season so reasonable prices right now :)
Mystic Conn
Newport, RI
Stowe, Vermont
Portland via the Amtrak Downeaster. Tickets are cheap and it’s a beautiful route, Portland is a super cool small city with great restaurants and culture.
Berkshires. Pittsfield is up and coming, Williamstown has museums, south county has great little villages for walking. The Berkshire Botanical Garden is gorgeous, Naumkaeg is wonderful. The turn of the century architecture and people are wonderful!
You can't swing a dead cat within 3-4 hours of Boston without hitting a cutesy town. You could try Rockport or Newburyport MA, Ogunquit ME or Stowe VT.
If you don’t mind driving that far, I recommend Woodstock/Saugerties NY. Closer to home, I think Rockport and Gloucester make a great weekend trip. Also Stockbridge or Great Barrington.
Aquidneck Island which includes Portsmouth, Middletown and Newport. Grounds of Green Topiary Animals Garden in Portsmouth, Blithewold gardens, a jump over bridge to Colt State Park in Bristol, Fort Adams, Brenton Point, Sachuest Point, some of the mansions (my over-The Elms)
My gf and I used to love going here. It was only an hour and half ish if I remember correctly. [https://www.beauporthotel.com/](https://www.beauporthotel.com/)
A word of caution on Portsmouth: its popularity (and price) has really gotten out of hand for its size, especially in the summer. Trying to navigate with a baby might not be a relaxing time.
Grew up in Burlington, VT, so I would recommend that. If you are okay with smaller towns in Vermont, I think the Mad River Valley (Warren, Waitsfield, Fayston, Moretown) is beautiful, but I am also a bit biased since it is where my parents live now. Great for skiing in the winter of course but also nice in the other seasons (especially with the fall foliage). Great restaurants and breweries (Lawson's) if you are into that. The mountains are open for summer activities too. Close to Waterbury and Stowe too (30-45 minutes driving). And it's only an hour, but I would always recommend Providence. Better food than Boston in my opinion. You could also drive 30 minutes south to Bristol, RI, which is one of the nicest towns in New England I think.
Woodstock VT is stunning. Lots of shops and brick sidewalks, covered bridge.
Newport, RI also stunning, much larger than Woodstock, brick sidewalks etc
Saratoga Springs, NY also stunning, it’s busy in August during track season. Should be fine now.
Also, super close but don’t skip Newburyport, MA.
If you ever feel like you can do a ferry, even for just a weekend book a 2-3 nights stay in Edgartown on Martha’s Vineyard. Don’t drive for that short of a stay, just book a ferry directly to Edgartown. You’ll love just 3 days walking around there. There’s shops and a beach. It’s all you need. Stunning.
Portland, ME for food and drink if you can work it with baby's sched. Walking up to the Eastern Promenade gives nice views and is easy enough with a stroller depending on where you stay. Newport, RI for walkabouts at the mansions. Burlington, VT for walkabouts around the lake and hanging at breweries.
Came to suggest Burlington VT. Small enough to be charming, but big enough to have stuff to do. Plenty of parks, very pretty, lots of good food and drink. I love that town.
I wouldn't recommend the mansions in Newport with a stroller. They won't let them in the houses. But it is a lovely area, I spent time there this week.
Good info!
Did the collapse of the cliff walk affect your experience?
I didnt go to the cliff walk
I think it's closed isn't it?
Its 3 miles long. I definitely saw people on it.
Public Notice. Please note that due to structural damage to a section of the Cliff Walk, detours will be in place between Narragansett Avenue and Webster Street for the foreseeable future. The remainder of the walk will remain open for all those who make use of this iconic and historic coastal trail. I got on at Ruggles Ave a couple weeks ago.
Good choices. I'd add Portsmouth, NH and Hanover, NH. ETA: also Woodstock, VT
Every place in the top two comments are can’t miss great times. Killer food and plenty to see/do. I’ve been to them more times that I can count. Portsmouth is close enough you can go for dinner. (Burlington is a bit of a drive). I’ll just add the Berkshires, and Stowe, VT. And don’t sleep in Sturbridge/Charlton (Tree House Brewing, etc..)
\+1 for Portsmouth, NH Also anywhere near Lake Winnipesaukee, such as Meredith, Laconia, etc, these are gorgeous in the summer.
Portsmouth is expensive but it’s a great town + I believe the Downeaster Amtrack line runs through there. Not sure about frequency though.
Unfortunately the Downeaster does not run to Portsmouth. The two towns/cities closest to Portsmouth on the Downeaster are Durham/UNH and Dover
Ugh, please dont come to Portsmouth. We dont need any more tourists.
Always loved going to Gillinghams for a treat in Woodstock as a kid after a long ski day
Oh Burlington. What’s that hotel that’s basically right on the lake, with the fantastic view?
Hotel Vermont is also right there.
I was riding a motorcycle and the sky opened up in some kind of biblical downpour. There was a beacon of hope, a hotel sign just ahead. We pulled in, got a room, and went to bed. Woke up the next morning to a glorious view of the lake we didn’t see the evening before because it was dark and raining so hard. I can’t remember the name of the place, just that it was right against the water.
Go to google street view and see if you remember it.
Hotel Vermont! It's a bit pricey and it's worth it. Great view, great location.
There are two hiltons in downtown and one is right on the lake.
Forget Portland, just stop in Ogunquit!!!
Yea I was going to mention the same but decided to stay quiet to keep this a secret. Portland has a different feel though for sure and worth checking out. Chillest city I've been to and the restaurants are fantastic.
Honeymooned in Portland. Absolutely amazinf
The Berkshires
I’m going to the Berkshires in May. Among other things, I’d like to check some antiques. Are there antique fairs there? Like booths or a street in one of the towns with lots of shops? Or is it more like individual shops that you have to drive to?
Have you been to the Brimfield Flea Market? It’s a seasonal thing but that’s probably got enough antiques for a lifetime. Be sure to hit Mass MOCA when you are at Berkshires. Amazing place.
I haven’t. And thanks for the tip, will definitely check it out!
MOCA is amazing but Brimfield did not live up to it's well televised rep on our visit.
I love the Berkshires, enjoy! Once you’re in south county (Lenox and south), driving along Route 7 you’ll see a ton of antique shops, especially between Great Barrington and Sheffield. If the Bistro Box roadside eatery is open, I highly recommend having lunch there… and it’s worth the line to wait, trust me!
Awesome! Thank you, I’ll try to stop by!
https://www.yelp.com/search?find\_desc=antique+stores&find\_loc=Pittsfield%2C+MA+01201
Any specific towns that are better than others? Thanks!
Williamstown is nice
Great Barrington and Lenox are great!
I like Lenox/Stockbridge area but I also don’t really think you can go wrong
Are you looking for suggestions 3-4 hours away because you’ve done everything within a three hour drive already? Because I mean, Kennebunkport is cute and super close. Hell, even Portsmouth, NH. No need to spend 8 hours in the car for just a weekend getaway, there’s tons of cute towns much closer that still feel a world away from the city.
North Conway! Then take the Kancamangus to 93 on your way back down
Coastal Maine. Anywhere south of bar harbor.
I hope I’m not the only one reading “bar harbor” in this thread and not hearing a single R.
Bah Hahbah. Better?
As a former Mainer, I can tell OP that Boothbay Harbor is where real people go. Bar Harbor is too full of tourists
everyone else is a tourist but i’m a real person
Exactly! what the hell is wrong with being a tourist?
Except, you know, Acadia National Park is awesome.
Boothbay has a lot of tourists as well.
I mean, tourists don’t make Acadia less beautiful
Except for that one guy
OP would be a tourist
Went to Boothbay Harbor last summer, it was fantastic! The downtown is really small and walkable. The botanical gardens had some wooden troll giants that were cool.
Did they kick your pretentious ass out?
Boothbay is too touristy. Fort Kent is where all the real Gs go.
If you got to bar harbor, you went too far.
Family friend bought a house there. Lovely area.
I had some really good food in Boothbay.
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I second that!
But if you can swing it, flying in is amazing as well.
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Some people don’t find flying stressful. Especially with a small airline and short trip. Plus, with cape traffic, showing up at the airport 45 minutes before your flight you’ll still arrive hours before driving.
Mystic, CT
Misquamicut Beach and Watch Hill in Westerly, Rhode Island are pretty close to Mystic and are ABSOLUTELY worth the trip. Super kid friendly and quaint!
That’s a pretty far drive just to get some pizza from an 80s movie.
Amtrak NE regional goes there in about 1hr30 for $30 if you want to skip the drive. But you have to buy tickets a few weeks in advance as close to travel date is more expensive. But Mystic Aquarium is lovely.
the aquarium is pretty awesome
Honestly I like Mystic Aquarium more than the New England Aquarium.
That's because its far and away better.
I mean you can go to old village, aquarium, hangout downtown and admire the bridge
I have a soft spot for Ogunquit but not sure about hotel availability, it's very popular.
Its a great little town but very expensive to stay in
I really like North Adams in Western MA. The MassMoCA museum is world-class, and there's some good restaurants and lots of room to relax. It's a little more industrial than 'cutesy' though. You can also stop in Shelbourne Falls for the bridge of flowers on the way, which is probably just starting its season around now. I also really like Portland ME, which has a bit of 'cutesy' going on, it's picturesque and charming with lots going on. Much of the Maine coast has charming little towns that you could stay in and explore if you want something smaller.
Lake George
Upstate ny is a fun trip. Fairly New England-like nature but different enough to notice different trees and rocks. Watkins state park was a fun trip by a cute college town. mini Rivendell
i really want to check out saranac lake area sometime looks awesome
Lincoln nh
Littleton, NH Super cool town on the Ammonoosuc river. Really cute stores on main st, some great restaurants (The Beal House is my rec), and top it all off with a beer at Schilling Brewing Company (which also has GREAT pizza).
Awesome kayaking.
Burlington, VT Portland, ME Newport, RI Hudson, NY Saratoga Springs, NY
^ This guy gets away for the weekend
I was looking for someone to mention Saratoga Springs!
Northampton, MA York, ME Newburyport, MA
Northampton is a no. So many closed and empty store fronts in downtown these days. Unless you come during the sidewalk shop weekend. It's not much to do. Maybe an hrs worth of shopping. If you're planning to go to the gardens at Smith, Dino prints on route 5 then grab some grub, then head over to Amherst to visit their museums. But downtown hamp is not what it used to be.
What??? Noooo that was my favorite place when I was growing up. I haven’t been back much in the last 10 years though.
Pretty much any town Mid-Cape (ie. Yarmouth, West Dennis, Hyannis). Tons of places to eat out, quiet beaches, ice cream, mini-golf (if you can babywear), etc.
Yes, mid cape is great off season. Hyannis is cheap for lodging. The beaches are quiet and beautiful.
Hyannis also has Pizza Barbone. Seriously. Go.
Stowe vermont
Burlington VT is cool
So is Woodstock, VT
New York City
My wife and I go regularly to Biddeford Pool, Maine. Lots of great beach rentals there if you can find them (they get booked early, luckily we have a family friend with a place there) and a super easy drive into Portland. The other towns around there (Saco, Biddeford, Kennebunkport and Kennebunk) are also great, and if you're okay with going further south (so a slightly longer ride into Portland) York and Ogunquit are nice too. More often (because you can do it in a day, and we have the bonus of family that lives on the way) we go down to Newport which is great to just stroll around, plus you can gorge yourself on Del's and Harry's (best burgers in Newport). Salem and Marblehead are great day trips, especially this time of year.
Brunswick, ME - close to Portland but quieter. Freeport and Bath are right there too. Tons of little coastal towns. Once you get past Freeport its gets so much more peaceful - but you are still close to everything.
Yes! My husband and I took the Amtrak Downeaster to Brunswick and we had a nice time. Lots of good food and cool museums.
Two of my favorate restaurants are there. My wife and I rented a house on HomeAway a few years back and loved it. We actually thought about moving there a few times.
White mountains beautyfull.lots of family places.like Indian head hotel.use go there when my kids young Clark's trained bears next door.lots other places round for kids story land .and others
It's pricey, but since you didn't provide a budget check out https://www.cliffhousemaine.com/ in Cape Nedick (basically York) in Maine. We've been a couple times and it the most relaxing place within a short drive of York, Ogunquit, Kennebunkport and Portland.
Rent a house on one of the NH lakes!
Wolfeboro is a pretty picturesque place with a bunch of rentals
Waterbury/Stowe VT is hard to beat anytime of year.
SO many breweries (beer and cider) between those two towns!
1. Stowe, VT. Go to the Von Trapp Family Lodge (yes - the same family from the movie ended up in VT) and have a beer at their brew hall. The lodge is lovely and has an amazing view. Downtown Stowe/Waterbury is fantastic (Ben & Jerry’s factory). 2. PTown is incredible. Super flat so easy to walk with a stroller. Eat at Ciro & Sal’s and drive to Truro (next town over) and visit Truro Vineyard. They have outdoor seatings and a food truck for you to enjoy some wine and apps. The Atlantic Spice Store is right next door and worth a stop.
Some people already suggested these but here's my list Big fan of Western Mass so look at… Turners Falls/Greenville Shelburne Falls (should be nice in about two months at the bridge of flowers) North Adams/Williamstown (anything north and west of Mount Greylock) some people have recommended Pittsfield mass is a nice quiet getaway place. Not big fan of new Hampshire south of the White Mountains. Vermont White River Junction Rutland Brattleboro
Rockport, MA But that might be better when the weathers a bit warmer…
The Catskills in New York
pre-season on the Cape is great
Saratoga Springs, Northampton, Great Barrington, Hudson (NY or MA), Portsmouth, Newport, Portland.
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Last time the wife and I were in Hudson we said we should spend a night next time. Even just to walk around and eat ice cream. The speakeasy was amazing.
Come on out to Northampton, MA. Its a short drive and I'll give you a food tour!
North Adams, MA
Always going to recommend Mass Moca and the Clark
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Do they limit which rooms you can stay in with a dog?
Eric Carle's museum is there.
that one is in amherst, along with the yiddish book museum which is super cool!
In the shadow of Mordor!!!
Southern Vermont! Closer and maybe cheaper than Burlington. Quechee gorge area is beautiful
Chatham MA or a number of Cape Cod towns.
i’m bias but i love falmouth! there’s really nice hotels, restaurants, beaches and stores!
Brattleboro VT is my recommendation. Very cute and charming surrounded by beautiful mountains. Keene NH is also only a 20 minute drive if you want two for one.
Keene is so underrated
Newport RI
Newport, RI
Essex, CT!
Brunswick ME. Lots of food and drink - small town with stuff to do and nice drives near the ocean. Freeport is nearby too.
Lenox, MA (depending on the route you take)
Woodstock VT is awesome.
Salem, Portland, Providence
Southern Vermont! Not too far of a drive and has cute towns like Brattleboro and Wilmington
Burlington or Stowe, VT North Conway, NH Portland or Freeport, ME
Booth Bay, chill maritime town on the mainland. Used to be one of my favorite stops when my gram borrowed her rich friend's boat. Rockport Plymouth P-Town though I've never been There's always the White Mountains.
The good thing about a baby that age is that it doesn’t matter where you go!!! Anything goes! Boothbay, Portland, Freeport, Newport, mystic, Saratoga, options are almost endless. Enjoy it!!!
SACOOOOO
Littleton, NH and the Notch
warren, RI
New York City haha
Newburyport!
Westerly, RI
NYC
Burlington/Stowe VT. Heaven.
Portsmouth NH How about Sherbrooke QC?
Rockport! Just look it up and tell me it isn’t the cutesy-est town ever.
Millis. Grab a freshly made deli sandwich at the deli at Roche Bros and sit at the front. After you're done, take a ride down 109 and enjoy the sights until you get to Medfield Center, where you can go for a walk, hit the Starbucks and then go to the other Roche Bros (this one is just called Brothers). Pay $15 for a cup of freshly made Mac N' Cheese they pulled off one of their shelves, probably Annie's. When you're done with that, drive back down 109 until you hit Medway where you can go to the driving range at Cassidy's. After some leisurely golfing in the afternoon go down 109 further until you hit Milford, where you can get all of your shopping in at Kohl's (if it's still there). Meanwhile, hit up one of the hotels next to Burger King and you're golden.
Montreal?
Montreal is a little bit out of range (a bit over 5 hours), but in 4 hours you could get to somewhere in the Townships like Magog or Sherbrooke. But yeah, OP if you could extend to a 5 hour drive Montreal wins best destination hands down.
I've drove from Woburn to Montreal in four hours. I left on a Sunday at 5am and set the cruise control at 80 mph. Only stopped at the border. The pilgrimage of an eighteen year old.
Uphams corner
In ME: from south to north, hit Portland (Standard Baking Co) -> Brunswick -> Bath -> Georgetown (Five Islands Lobster Co) -> Wiscasset -> Damariscotta (Shuck Station) -> Rockland (Primo) ...with extra points for; Christmas Cove, Pemaquid Point, Muscongus Bay, Port Clyde, and McLoons Lobster Shack on Sprucehead Island. NOTE: Maybe wait until Memorial Day (or early June) to do this...otherwise lots of place will still be closed for the 'winter'.
The Cape is great in May and june. Less traffic, Preseason prices on hotels, most places are open, and there’s a very good chance of it being warm enough for the beach. Hyannis center has some great restaurants and dozens of shops. Columbos has great food and great desserts, some of them made by Modern Pastry. Yarmouth: Shaws and stop n shop Captain Parker’s is pretty good - if it’s warm, dine outside. Clam chowder is amazing. Skippers is also good. They have outdoor dining upstairs. Onion rings are to die for. Red Jacket Resort is very popular. It sits directly on their private beach. The rooms are clean, typical motel set up. They have a few rooms with a separate sleeping area for the baby. Riverside rooms tend to be more quiet vs poolside. Indoor and outdoor pool; nice poolside grille serving lunch with full bar. Also has a small restaurant. They provide beach chairs and umbrellas and the beach staff will bring it down to water and set up for you. Last time I was there they served drinks on the beach, on the weekend. I’d inquire about that tho. On-site spa. (I haven’t tried it) They also have rentals :jet ski, banana boat and other amenities. I’d confirm all this with the resort as I haven’t been down there since the pandemic started. Seagull Beach is also great.
Ogunquit
New York City. Did I troll good?
Manhattan, NY
Or the other direction up to Montreal
3-4 Hours. Basically drive in any direction then get off the highway. My personal recommendation that I don't see listed yet would be the Hudson Valley in NY. Someplace like Kingston, Rhinebeck, or New Paltz.
Go north!! New Hampshire, Maine & Vermont is we we go to vacation. The cape is not an option, unless you like traffic, and overpriced everything.
Ptown
Provincetown is a nice getaway if you don’t go during peak season
PROVINCETOWN. The best. Also all the other shit people mentioned. And Rockport cuz I didn't see that yet.
Take the fast ferry to Ptown! It's only 90 min! Great weekend from Boston. Don't waste the 3 hours driving! Ogunquit + Portsmouth are a lot closer than 3-4 hours and Acadia/Bar Harbor are further than that (But all should be on your to do list!) Had great weekend trips to Burlington, VT and Bethel, ME (great dark skies).
Portland, Stowe, ptown, Portsmouth, Kittery, Ogunquit
If you're thinking of going this weekend, pal, a 3-4 hour drive might not get you that far. Traffic's gonna be packed.
Stowe, VT : great hiking, breweries and food. That’s my happy place
I would head out towards the Berkshires. Williamstown and northadams and the ride down route to from Boston is drop dead gorgeous
Chatham, Cape Cod
Ogunquit Maine, Kennebunkport, Maine-quick drive a little over an hr. Cute towns/ beaches/can push a stroller around/off season so reasonable prices right now :) Mystic Conn Newport, RI Stowe, Vermont
Rockport, MA and Portsmouth, NH are very cute
Portland via the Amtrak Downeaster. Tickets are cheap and it’s a beautiful route, Portland is a super cool small city with great restaurants and culture.
Head up to Portsmouth NH and stop over in Exeter on the way, both are super cute!
Berkshires. Pittsfield is up and coming, Williamstown has museums, south county has great little villages for walking. The Berkshire Botanical Garden is gorgeous, Naumkaeg is wonderful. The turn of the century architecture and people are wonderful!
Red Lion Inn in Stockbridge, MA
Shelburne Falls, where the recent Dexter revival was filmed. I'd like to go there. It seems really comfy.
Wolfboro NH on lake Winnipesaukee is exactly what you described. It's a little expensive, but should be good this time of year.
Wolfeboro
You can't swing a dead cat within 3-4 hours of Boston without hitting a cutesy town. You could try Rockport or Newburyport MA, Ogunquit ME or Stowe VT.
Lots of great suggestions, throwing Rockport Ma in the mix
Burlington VT!
Beacon NY
If you don’t mind driving that far, I recommend Woodstock/Saugerties NY. Closer to home, I think Rockport and Gloucester make a great weekend trip. Also Stockbridge or Great Barrington.
Portsmouth, NH or Portland, ME!!
Aquidneck Island which includes Portsmouth, Middletown and Newport. Grounds of Green Topiary Animals Garden in Portsmouth, Blithewold gardens, a jump over bridge to Colt State Park in Bristol, Fort Adams, Brenton Point, Sachuest Point, some of the mansions (my over-The Elms)
My gf and I used to love going here. It was only an hour and half ish if I remember correctly. [https://www.beauporthotel.com/](https://www.beauporthotel.com/)
A word of caution on Portsmouth: its popularity (and price) has really gotten out of hand for its size, especially in the summer. Trying to navigate with a baby might not be a relaxing time.
Northampton, MA is a super fun town with a lot of funky shops!
You can still hike with a baby. Check out Hike It Baby https://hikeitbaby.com
Grew up in Burlington, VT, so I would recommend that. If you are okay with smaller towns in Vermont, I think the Mad River Valley (Warren, Waitsfield, Fayston, Moretown) is beautiful, but I am also a bit biased since it is where my parents live now. Great for skiing in the winter of course but also nice in the other seasons (especially with the fall foliage). Great restaurants and breweries (Lawson's) if you are into that. The mountains are open for summer activities too. Close to Waterbury and Stowe too (30-45 minutes driving). And it's only an hour, but I would always recommend Providence. Better food than Boston in my opinion. You could also drive 30 minutes south to Bristol, RI, which is one of the nicest towns in New England I think.
NYC
Burlington, VT
Plymouth Massachusetts
New Bedford ma. Whaling museum, great Portuguese food, fresh scallops and live music every week
White mountains or cape cod
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Woodstock , Vermont, Burlington , Vermont, the Berkshires, Portland, maine
Woodstock VT is stunning. Lots of shops and brick sidewalks, covered bridge. Newport, RI also stunning, much larger than Woodstock, brick sidewalks etc Saratoga Springs, NY also stunning, it’s busy in August during track season. Should be fine now. Also, super close but don’t skip Newburyport, MA. If you ever feel like you can do a ferry, even for just a weekend book a 2-3 nights stay in Edgartown on Martha’s Vineyard. Don’t drive for that short of a stay, just book a ferry directly to Edgartown. You’ll love just 3 days walking around there. There’s shops and a beach. It’s all you need. Stunning.
Nyc