Boston to Brattleboro: Scenic routes/suggestions?
September 18, 2015 10:20 AM   Subscribe

We are planning a quick 2-night getaway trip to Brattleboro, leaving from North of Boston. I'd love your help choosing a route that will be scenic to drive, but not too too long, and also your recommendations for interesting, quirky, fun stops between here and there, and/or things to do while based there. We enjoy history, food, drink, farming, music, vintage/flea stuff, Americana, hiking, canoeing, etc. We've never spent time in the town before and will be staying right downtown. Thank you!
posted by Miko to Travel & Transportation (15 answers total) 7 users marked this as a favorite
 
Are you taking route 2 west? As far as highways go, it's very pretty, but there's not much there. Barton Cove is a pretty stop.

About when you reach 91, which goes right to Brattleboro, you'll be in Greenfield. If you're there around lunch, maybe stop by the People's Pint, a local brewpub.

Not enough beer? Lefty's brewery is there and they do tours on Saturday. I've met Lefty himself. He's really nice and makes good beer.

Head south and you're in Historic Deerfield. A little further south, you're at Magic Wings, a butterfly conservatory. Not far from there is Sunderland, where you can go up Sugarloaf and get a nice view of the pioneer valley and you're near Mike's Maze.

Still not enough beer? If you're in that area at 1:00PM, you can take a tour of the Berkshire Brewing Company. Again, nice folks, nice beer.

Also there's the Bridge of Flowers in Shelburne Falls.
posted by plinth at 10:40 AM on September 18, 2015 [7 favorites]


Response by poster: Are you taking route 2 west?

It depends - Google Maps gives 3 major options, and we're willing to detour for some fun moments. So I am flexible on exactly which way to go and love scenic routs and backways. I have driven Route 2 as far as North Adams before, though.
posted by Miko at 10:42 AM on September 18, 2015


Go west on Rt 2 - then there are 2 ways to go up 140 and rt 9 though Keene, NH or Rt 2 to 91. I would go 140 on the way there and come through Greenfield on the way back (or vice versa).

When you come home stop at the Montague book mill - open every day until 6. Terrific old mill with used books and restaurant. Great coffee and beer and food...

You could alter your route and go up 31 though Peterborough (what a great town). If you go that way and it's around lunch time you could go to Pickity place. It's a little farm with a story book house that serves lunch. They have 3 seatings. It's pretty adorable and very reasonable.

In Brattleboro, I would look into going to TJ Buckleys and Peter Havens for dinner. You'll want reservations.
posted by ReluctantViking at 11:05 AM on September 18, 2015 [1 favorite]


If you do go Route 2, the Bridge of Flowers (and Shelburne Falls in general) is definitely worth the stop.

However, seeing as you've done Route 2 before, I'd north up 140 and 12 (the most northerly route google gave) to 9, which is lovely. Or at least I've been on 9 a little west of Brattleboro, and it was gorgeous.

Keene must have great stops, too. Or if you wanted to go off track a little and head north sooner, Peterborough definitely has lots of art galleries and such.
posted by ldthomps at 11:07 AM on September 18, 2015


If you're there on a Saturday morning, the Brattleboro farmers' market is really wonderful. Not for the veggies, but for the prepared food! I'm sure the veggies are nice too.
posted by kelseyfrost at 11:54 AM on September 18, 2015


I used to drive that route a lot.
- On Route 2, I personally find just not stopping and getting it over with is the best approach
- For hiking in Brattleboro, there's the hike up Wantastiquet which maybe takes 90 minutes and offers good people watching on the way up and nice view of the area from the summit
- Nearby Putney is a nice place to check out when you're in the area--lots of cool shops (Putney Coop, the bike/ski shop along the highway, old books, antiques, etc.)
- Brattleboro (or Putney, I can't remember which) has an enormous Farmer's Market with a bunch of cultural stuff in addition to farm stuff.
- For food, I've found pretty much everything in Brattleboro is good--Indian place, Sushi, the cult'y vege place that offers famous "Square Deals"
- The drive from Brattleboro West along route 9 (toward the very expensive Vermont college who's name I can't remember) has a lot of what you're looking for along the way and is really scenic in its own right.
posted by Jon44 at 12:05 PM on September 18, 2015


I suggest getting off Route 2 at the Concord Rotary and taking MA-119 (initially concurrent with MA-2A, which breaks away just before I-495 in Littleton). MA-119 crosses into New Hampshire and becomes NH-119, which crosses into Vermont and becomes VT-119 for less than a mile before you hit US-5 in Brattleboro. It's kind of "the road less traveled." Willard Brook State Forest in Massachusetts was a particular favorite of mine as far as scenic areas go.
posted by tckma at 12:41 PM on September 18, 2015 [1 favorite]


If you decide to take Route 119, you MUST stop at Kimball Farm in Westford. I'm fairly sure this is a rite of passage for any Massachusetts resident, so you may have already been there.
posted by tckma at 12:45 PM on September 18, 2015 [1 favorite]


If you are going this weekend, you might consider a trip from Brattleboro up to the Tunbridge World's Fair.
posted by baseballpajamas at 12:49 PM on September 18, 2015


If you do take route 140 and 12 up through Keene, stop at the intersection of Route 12 & 202 in Winchendon and see the giant rocking horse! Downtown Keene is lovely (keep an eye out for the Parrish Shoes sign left over from the town's big hollywood moment in Jumanji) and route 9 between Keene and Brattleboro is a beautiful drive. Chesterfield Gorge is right along that stretch.

But if you only make one stop on that route between Boston and Brattleboro, it should be to visit the ruins at Madame Sherri's Forest, also a little ways off of route 9.
posted by usonian at 1:59 PM on September 18, 2015


I suggest getting off Route 2 at the Concord Rotary and taking MA-119 (initially concurrent with MA-2A, which breaks away just before I-495 in Littleton). MA-119 crosses into New Hampshire and becomes NH-119, which crosses into Vermont and becomes VT-119 for less than a mile before you hit US-5 in Brattleboro. It's kind of "the road less traveled."

I like this route. I have family who live near the rotary (well, 4-5 miles away) and I love bumbada bumbada-ing dow that way. Kimball Farm is where I used to go get ice cream when I was a kid, it's SCENEY now, but still a pretty good time and has a lot of good ice cream.

I've also done the 140 trip and it's also lovely. It goes through Princeton MA which is where the ancient Wests were from, so I always wave. And I know I sound like a broken record on this topic but the Brattleboro Public Library is also pretty much right downtown and doesn't look like much from the outside but it's got a lot of really neat art on the inside, oild local stuff (you can ask the librarian for a flyer that tells you what it all is) and is also a good place to pop in and check email. The downtown area of Brattleboro is great, just a lot of stuff that is walkable in every direction. You can't go wrong with anything, I like getting coffee at Mocha Joe's and Amy's Bakery has tasty stuff (and coffee).

Chesterfield is right across the river and has this weird thing that I've never managed to go and see which is also the place usonian points out.
posted by jessamyn at 2:46 PM on September 18, 2015 [1 favorite]


If you do go Route 2, the Bridge of Flowers (and Shelburne Falls in general) is definitely worth the stop.

Note that Shelburne Falls is actually west of Greenfield, so you'd be going a bit out of your way to do it — the most direct route would have you turning north on I-91 or US-5 at Greenfield. I do agree that Shelburne Falls is quite nice, though, and might be worth a detour if you have the time.
posted by Johnny Assay at 7:42 AM on September 19, 2015


In Brattleboro, I'd recommend a pint at McNiell's and dinner at Three Stones (amazing Mayan food a little off the beaten path--you need a reservation here) with the walk in between the two. The hike up Wantastiquet is also amazing--a shortish walk up switchbacks with a great payoff at the top! Bring picnic foods from the co-op.
That's my quick rundown of favorite things to do with visiting folks. Have fun!
posted by zem at 9:07 AM on September 19, 2015


Response by poster: Thank you SO much everybody. Right after I posted, I got the bad news that the online reservation form I'd used to book my stay was defective and that, in fact, the place was already full. Damn! But we'll plan another try soon, now that I know all about these great things to do. Thanks for the recommendations - can't wait to check this stuff out!
posted by Miko at 6:05 PM on September 19, 2015


Seconding the McNeil's recommendation. Also, I hope you're staying at the Latchis, which is one of my favorite hotels in North America.
posted by brand-gnu at 7:23 PM on September 19, 2015 [1 favorite]


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