30 minutes to Everywhere!
Food
Check out some of our favorite places to eat in Chatham and the surrounding area.
Everything is delish, but the Goodness Breakfast Sandwich is the best!
Check out their menu https://www.mainstgoodness.com/menu
Order online and pick up when you arrive or eat in at the cafe. The perfect place to start your day in Chatham.
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Main St Goodness, home of PieconicNY bakery
20 Main StEverything is delish, but the Goodness Breakfast Sandwich is the best!
Check out their menu https://www.mainstgoodness.com/menu
Order online and pick up when you arrive or eat in at the cafe. The perfect place to start your day in Chatham.
A delightful dinner spot. Enjoy a nice date or a meal with friends.
Check out their nightly deals! https://www.thepeoplespub.com/
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The People's Pub
36 Main StA delightful dinner spot. Enjoy a nice date or a meal with friends.
Check out their nightly deals! https://www.thepeoplespub.com/
The most unbelievably delicious bread and pastries. Featured in the documentary, "Cooked", on Netflix.
Two locations. One in Housatonic and another in Pittsfield, MA. The Pizza Cafe in Pittsfield has excellent sandwiches and "take and bake" pizza.
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Berkshire Mountain Bakery Inc
367 Park StThe most unbelievably delicious bread and pastries. Featured in the documentary, "Cooked", on Netflix.
Two locations. One in Housatonic and another in Pittsfield, MA. The Pizza Cafe in Pittsfield has excellent sandwiches and "take and bake" pizza.
Wonderful spot for coffee & breakfast. Sit and read or get some work done.
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No. Six Depot Roastery & Cafe
6 Depot StWonderful spot for coffee & breakfast. Sit and read or get some work done.
Good bar food. Trivia on Monday nights at 7 pm.
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Michaels of Stockbridge
5 Elm StGood bar food. Trivia on Monday nights at 7 pm.
Enjoy a beautiful meal at one of the most popular restaurants in Hudson!
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Hudson Food Studio
746 Warren StEnjoy a beautiful meal at one of the most popular restaurants in Hudson!
The Red Lion Inn
30 Main StHistoric Inn. Beautiful setting.
Blueberry Hill Market Cafe
515 US-20Yummy breakfast & lunch!
Bartlett House
2258 NY-66Delicious breakfast and lunch. Cute cafe.
Beautiful place to enjoy a meal. Sit upstairs in the wrap around enclosed porch or downstairs in the cozy bar area.
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Blue Plate
1 Kinderhook StBeautiful place to enjoy a meal. Sit upstairs in the wrap around enclosed porch or downstairs in the cozy bar area.
Excellent pastries and coffee for breakfast, yummy salads and sandwiches for lunch. Take some of the bread to go!
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Our Daily Bread Deli
116 Hudson AveExcellent pastries and coffee for breakfast, yummy salads and sandwiches for lunch. Take some of the bread to go!
If you’re looking for great ambience and great food, this is the place! It is pricey so save for a special night out.
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Rivertown Lodge
731 Warren StreetIf you’re looking for great ambience and great food, this is the place! It is pricey so save for a special night out.
Excellent food, nice decor. Great spot for a celebratory dinner only 20 minutes from our house!
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Local 111
111 Main StExcellent food, nice decor. Great spot for a celebratory dinner only 20 minutes from our house!
Grab a quick sandwich or some items for your charcuterie board!
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Bimi's Cheese Shop
21 Main StGrab a quick sandwich or some items for your charcuterie board!
Great spot for dinner. Enjoy sitting by the beautiful bar downstairs. Great cocktails and mocktails.
Bimi's Canteen & Bar
Great spot for dinner. Enjoy sitting by the beautiful bar downstairs. Great cocktails and mocktails.
Haven
8 Franklin StDelicious breakfast! Often has a line, but it moves quickly.
Breweries
Great beer and food! An excellent place to watch a game. Buy some cans to go!
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Chatham Brewing
59 Main StGreat beer and food! An excellent place to watch a game. Buy some cans to go!
Great beer selection, live music, and a food truck outside!
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Hudson Brewing Company
99 S 3rd StGreat beer selection, live music, and a food truck outside!
Barrington Brewery & Restaurant
420 Stockbridge RoadGreat beer & food!
Hiking
The highest waterfall in Massachusetts, just 30 mins away! Great hiking trails throughout the state park.
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Parco Statale Bash Bish Falls
Falls RoadThe highest waterfall in Massachusetts, just 30 mins away! Great hiking trails throughout the state park.
Excellent hiking right down the road from our house.
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Beebe Hill State Forest
County Route 5Excellent hiking right down the road from our house.
Olivia's Overlook
Hiking TrailsBeautiful hiking trails!
Wineries
Balderdash Cellars
81 State RdBeautiful setting to sit and sip. Live music.
Enjoy sitting outside during the summer or inside in the winter. Great wine!
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Cantina Hudson Chatham
1900 NY-66Enjoy sitting outside during the summer or inside in the winter. Great wine!
Arts & Music
The summer home for the Boston Symphony Orchestra, this venue also hosts several big names per summer! A beautiful place to see a concert from the lawn.
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Tanglewood
The summer home for the Boston Symphony Orchestra, this venue also hosts several big names per summer! A beautiful place to see a concert from the lawn.
Naumkeag
5 Prospect Hill RdGarden & historic home.
Giardino Botanico di Berkshire
5 W Stockbridge RdCrandell Theatre
48 Main StCool local movie theater.
Jacob's Pillow
358 George Carter RdDance venue in the Berkshires. Beautiful setting.
Ski & Snowboard
Check out the Mountain Adventure Park & Hiking in the summer or ski & board in the winter.
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Jiminy Peak
37 Corey RdCheck out the Mountain Adventure Park & Hiking in the summer or ski & board in the winter.
Ski Butternut
380 State RdSki, snowboard or tube. Great family mountain.
Small mountain, good for beginners or families. Ski, snowboard or tube.
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Bousquet Ski Area
101 Dan Fox DrSmall mountain, good for beginners or families. Ski, snowboard or tube.
Aerial adventure park in the summer, ski & snowboard in the winter.
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Catamount Mountain Ski Resort
78 Catamount RdAerial adventure park in the summer, ski & snowboard in the winter.
Parks
Onota Lake
Lakeway DriveGreat for picnics and swimming!