Things To Do
Hy's Fried
Fried chicken spot with drinks and dj/dancing - *very close to the venue, although technically not in Hillsdale.
Roe Jan Brewing Co.
Great local beer, elevated pub fare, and a super fun vibe.
Little Apple Cidery
Local Cider with lawn chairs and outdoor tables in the center of an orchard - dog friendly : )
Vine Gate Lavender Floral Farm
U Pick Lavender Farm with farm store
White Oak Farm
Local Farm Stand with seasonal produce + top secret BBQ sauce (shh)
Harlem Valley Rail Trail
Bike, Walk, or roller skate on the rail trail!
Copake Hillsdale Farmers Market
Saturday mornings (9 am-1 pm)
Roeliff Jansen Park (Roe Jan Park)
Great place to go walking. Dog run!
Hillsdale House Restaurant
American fare in a historic, welcoming 1797 Tavern + wood fired pizzas
Twisted Sisters Coffee House
Coffee and small bites
Four Brothers Pizza Inn
Pizzaaaaaa
Rodgers Book Barn
Old and Unusual Books
Catamount Mountain Resort & Zipline
Zipline!!!!!
LABspace
~~art gallery~~
Little Cat Lodge Restaurant
amazing cocktails and exciting, fun seasonal dishes.
The Egremont Barn
live music venue in an old barn - food, drink, outdoor space!
Mom's Country Cafe
mom 'n pop diner on a creek - serving breakfast and lunch
Appalachian Trail
Take a hike! ;)
Bash Bish Falls Trail
Hike & Swim at Bash Bish Falls - 1.6 out and back on gravel path to tallest waterfall in MA
Copake Wine Works
~wine shop~
Copake General Store
Fantastic provisions -- and made-to-order sandwiches (love the bahn mi!)
The Greens at Copake Country Club
A cozy dining room situated around a retro 360 degree fireplace - brunch, happy hour, dinner
Zinnia’s Dinette
Rhode Island- style fish fry and inspired salads and sides and soft serve
Random Harvest
A wonderful local market and grab-and-go food shop. Also has coffee.
Sideshow Vintage Clothing
Copake Lake Boat & Ski
Rent a boat, stand up paddle board or kayak. Check out the bar & Restaurant with live music.
Jackson's BBQ, Beer, Ice Cream
Really, Really good.
Cooper's Daughter Spirits
Sip local spirits around a firepit at Old York Farm
The Stagecoach Tavern at Race Brook Lodge
Restaurant, cafe, music venue with trails and waterfalls on property
Norman Rockwell Museum
Significant collection of the artist's original work & memorabilia on display in his hometown.
Laura's Tower Trail
1.8 mile out and back trail - gradual climb through pine and birch trees to a tower with great views
TurnPark Art Space
Outdoor sculpture park featuring works from the 1970s and live performances.
Great Barrington (Walk, shop and eat in this nearby town)
Soco Creamery
most renowned ice cream in all the land
Monument Mountain Reservation/Flag Rock Trailhead
Popular hike at Monument Mountain - Flag Rock + Summit Trails are both great (moderate 3.5/4 mile hikes)
Berkshire Mountain Bakery
~ Best bakery in the region ~
Barrington Brewery & Restaurant
Brewery and Restaurant with outdoor seating
Guido's Fresh Marketplace
Fully stocked supermarket for anyone staying in Great Barrington
Pleasant and Main Cafe General Store
cafe & restaurant with homey interior - if you are staying in Great Barrington, it's a short drive
Art Omi
Outdoor Sculpture Park
Hudson (Walk, shop and eat in this nearby town)
Lil' Deb's Oasis
Tropical comfort food & craft beer served in a playful, arty space with counter stools and a retro feel.
Kitty's
"Kitty’s Restaurant and Bar is the Hudson Valley dinner party that everyone is invited to."
feast & floret
Flower shop + Italian inspired Restaurant + Wine
Cafe Mutton
award winning spot with brunch and dinner options
Quinnie's New York
Sandwich shop
Wm. Farmer and Sons
cozy, coppery barroom and restaurant features craft cocktails, light bites and seasonal dishes
Four Brothers Drive-in Movie
It's a drive in movie theater!