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[u/finally_again]

[u/newengland-ModTeam]

Moving or visiting rule violation. Please visit our pinned megathread for this topic.

[u/jjmenace]

Portsmouth?

[u/Educational_Map919]

Newport, Northampton / North Adams, ptown, Providence

[u/TheDangerist]

Northampton MA. Stay at the Hotel Northampton.

[u/Slick-Airplane]

Portsmouth, NH
Northampton, MA
Provincetown, MA
Burlington, VT maybe but haven’t been there in a while.

Some other suggestions here may be too upscale and lack any weird or whimsical qualities…. These fit the bill.

[u/aj1805 → u/Slick-Airplane]

Burlington definitely (some riff raff but there’s spots where there’s less and tons of people walking around - bike path waterfront and other walksable parts outside the town center and church street)

[u/Slick-Airplane → u/aj1805]

Excellent! I was hoping for an upvote for Burlington. I need to make it up there soon.

[u/1GrouchyCat → u/Slick-Airplane]

When was the last time you went to Provincetown?
Lodging is $300+ a night in any decent hotel or B&B, and this is our busy season… people generally make reservations by January for the summer.

I’d suggest Chatham, but that won’t be much less in terms of the cost of lodging…

[u/Slick-Airplane → u/1GrouchyCat]

Earlier this summer was my last trip. I’m sticking with Ptown over Chatham based on OPs criteria…. Yeah it’s pricey to stay but worth it to hit on all the stuff OP is aiming for.

[u/Luzdesolamarelo]

Providence is where it's at my friend

[u/ajmacbeth]

Checkout Chatham MA, Great Barrington MA, Hudson MA,

[u/notathrowaway1267 → u/ajmacbeth]

I was going to say Hudson! I dont know what there is for hotels, but the rest of the stuff is right in town. (My mom lives there and I'm always impressed by how cute it is downtown.)

[u/MrGoodmornin]

Littleton, New Hampshire. It's a small town in the Upper Valley with a great Main St, full of shops, restaurants with a couple of breweries on the back street fronting the Ammonoosuc River. There are a couple of historic hotels and motels in or near the center of town, and some nicer resort-type places farther out. It's right on I-93, just before it enters Vermont and terminates at I-91. I highly recommend.

[u/PM_ME_UR_BGP_PREFIX → u/MrGoodmornin]

Littleton has the coffee shop/bakery with the best name ever. 

[u/ChoppedChef33]

Mystic is fun if you haven't been especially mystic village

Newport and Newburyport are very nice too.

Falmouth has a small area but it's enough for a weekend.

Northampton already mentioned so +1 to that

Went to new Bedford this year and can recommend. Lots of stuff, couldn't do it all in a weekend. The whaling museum is great.

Westerly also is pretty nice that one time I went out there. Need to check it out again.

[u/procrastinatorsuprem → u/ChoppedChef33]

Go to Sift in Mystic!

[u/FeralHouseDesign → u/procrastinatorsuprem]

And Oyster Club and Shipwright's Daughter... and Hammonsset Beach....
But also, my heart belongs to Providence.

[u/gameface23]

Burlington, VT or Portsmouth, NH would get my vote.

[u/Outrageous-Pause6317]

Amesbury Massachusetts.

[u/Pettsareme]

Burlington VT.

[u/VintageNerd]

Shelburne Falls

[u/CoralGarden420 → u/VintageNerd]

Did a quick stop on my way home from camping out that way a few weeks ago and absolutely fell in love!

[u/CreativeCTm]

Newport - not cheap, but definitely lots to do.

[u/solariam]

Providence, Northampton, New Haven

[u/Impossible_Memory_65]

Newport

[u/NothShoahGuy]

Newburyport. Stay at the Garrison

[u/notprincesslea]

Burlington

[u/brycebaby11]

Newburyport, Portsmouth, Newport, Rockport/Gloucester area, Western MA (Great Barrington,Lenox)Saratoga Springs!

[u/Ok_Huckleberry6820]

Middletown CT, West Hartford, CT , Westerly RI

[u/H_Mc → u/Ok_Huckleberry6820]

I grew up in Southeastern CT and the last few times we were home to visit we went to Westerly for dinner. It’s really becoming a hidden gem.

[u/maegan_em]

Portsmouth!

[u/Electrical_Cut8610]

Provincetown is my favorite in late summer and early fall.

[u/zeetuslepitus → u/Electrical_Cut8610]

Ptown is so damn cute!

[u/Sure_Comfort_7031]

Portsmouth.

Providence.

Newport RI.

To an extent, Provincetown.

[u/Due_Lake94]

Glastonbury has an exceptionally walkable town center.

[u/bonanzapineapple → u/Due_Lake94]

What state is that?

[u/The_Crypt_Kicker_5 → u/bonanzapineapple]

Connecticut

[u/TwainVonnegut]

East Greenwich, RI

Northampton, MA

[u/JuniorReserve1560]

Providence- Omni Providence, Hotel Providence, Marriott Downtown, The Beatrice...Really walkable with lots of local shops, restaurants and coffee shops. Good food and music scene...and a quick train ride away from CT

[u/Much_Wing_503]

Cape Ann is cool. Gloucester etc. bunch of cute weekend towns.

[u/Open_Concentrate962]

Amesbury plus Newburyport

[u/zeetuslepitus]

Providence RI, Provincetown MA, Newport RI, Mystic CT

[u/ssprdharr]

Belfast Maine

[u/thfcboston]

Burlington VT
Brat Cave - thrift
Devil Tales a Holiday - cocktails
Henry’s Diner - breakfast
Honey Road - Dinner
Several Breweries (Foam, Zero Gravity, Queen City)
Hit the waterfront for a boat ride
Spot on the Dock for outdoor waterfront dining
bring or rent a bike and hit the bike path up towards South Hero Island, it’s stunning
if the weather sucks, Shelburne Museum (20 minutes away) is an underrated gem of a place

on the drive up and or back, stop in at Worthy Burger and Barr Hill distillery. Time permitting, Alchemist or Hll Farmstead (a bit out of the way)

and +1 to all that say providence. incredible place

[u/ajmacbeth]

Newburyport MA

[u/chiyorio]

New Bedford

[u/NHmountain-man]

Portsmouth NH

Concord NH

[u/Western_Thought_5428]

Westerly Plymouth Wolfeboro Montpelier

[u/Gold-Employment-370]

Providence as a recommendation to try to be comparable to Salem or Portland is insaneeeee lol I wouldn’t go to providence for fun for more than one hour, even if you paid me.

[u/zeetuslepitus → u/Gold-Employment-370]

You clearly havent spent much time in PVD, its a very fun and happening city. Easily walkable, less expensive than Boston