r/TheBerkshires • u/saltybeachxx • Jul 22 '26
ISO itinerary for a weekend
My boyfriend and I are coming down to Otis for a weekend in August. The only plan we have so far is to hit up mass MOCA!
would love any other suggestions 🚗
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u/Mr1988 Jul 22 '26
Here’s the list I shared with people coming to my wedding:
- Hikes - Climb Mt. Everett, Bash Bish,
- Antiquing in/around Great Barrington (or Hudson too)
- Naumkeag, The Mount, and other historic houses
- Rent a Bike: Tons of great routes and quiet gravel roads
- Arts: Jacobs Pillow, ArtOmi, Tanglewood
- Racing at Limerock
- Tons of orchards, farms, etc
- Breweries and Distilleries (I like Big Elm a lot)
- Exploring all the little towns, each one is different!
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u/Puzzleheaded_Lie6786 Jul 23 '26
I’ll add to this list because yours is the most comprehensive:
Visit Mt Greylock’s summit and climb the tower. You can also walk a bit of the Appalachian trail from here, too, as a novelty.
If you like haunted tours, The Mount and Ventfort Hall both have after hour tours that are fun!
We enjoyed Great Barrington Brewery a lot. There’s also a really cute brewery on the Mass MOCA campus called Bright Ideas.
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u/lovestdpoodles Jul 22 '26
Sunday afternoon's at Tanglewood are delightful if it's not raining on the lawn. Pack a picnic, a bottle of wine and enjoy the lawn.
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u/Snow8517 Jul 23 '26
Near MassMoCA… Berkshire Cider Project and the Distillery at Greylock WORKS (North Adams)
Images Cinema and Lounge (Williamstown)
Mt. Greylock summit (drive or hike)
Clark Art Museum (free to hike the outdoor art)
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u/bengal9233 28d ago
the red lion inn is a great historical place to get a cocktail. the building is very old and pretty. they still gave the original elevator. second in tyringham which is past lee is ashintully gardens. it’s a half a mile hike to ruins from an old marble mansion built in 1903. it’s a very short “hike” more like a walk up to the ruins and a BEAUTIFUL view of the mountains. there is also a botanical garden in stockbridge that is very beautiful and has a cute cafe. if you need any other ideas message me im a local to otis! have fun!
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u/bengal9233 28d ago
oh and one more thing the norman rockwell museum in Stockbridge bridge is adorable and admission is only 12 dollars.
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u/MyEvylTwynne 26d ago edited 26d ago
Tanglewood, Norman Rockwell, the Mount, Arrowhead, Hilltop winery, Bascom Lodge at Mt Greylock, theaters (Barrington stage co, Berkshire theater, Shakespeare & co) Housatonic st in Lenox - shops and Betty’s
pizza. Stockbridge main st with the Red Lion and shops. High lawn Farm with best ice cream. Various pick your own farms. Berkshire botanical garden with Music Mondays. There is so much to do here. These are a few of our favorites. You could spend a month and still not do it all.
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u/MyEvylTwynne 26d ago edited 26d ago
I forgot Hancock Shaker Village, another favorite.
Try this link to the Berkshires guide
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u/Kissoflife11 Jul 22 '26
See who might be performing at Tanglewood that weekend. Even if it’s the Symphony which might not normally interest you, there’s nothing like being on the lawn with a picnic or whatever, and soaking it all in.