In partnership with Prospect Berkshires
I was recently invited to spend a few days with my family at Prospect Berkshires, just a few hours’ drive from Park Slope. The Berkshires is one of my favorite regions, with great dining, wonderful art museums, and plenty of opportunities to slow down and enjoy the surrounding nature and mountain scenery.
You can see all these places on a Google Map at the end of the article too!
Where to Stay: Prospect Berkshires
One of the Berkshires’ newer stays, Prospect Berkshires is especially worth having on your list for fall. Upon arrival in the parking area, the staff help you with your baggage and take you directly to your cabin on a golf cart. You’ll pass some of the complementary recreational facilities like the pool (which our kids immediately visited after leaving bags at the cabin), cold plunge, pickleball courts, kayaks & paddleboards, bikes, and saunas.
In the quiet Knoll Cabin, there were lots of little touches I appreciated too - coffee from Irving Farm Coffee Roasters and Rishi tea, along with beautiful natural materials. I loved the feeling of being completely surrounded by the woods - from the smell of pine when we walked into our cabin to the thoughtful design that makes the cabins feel like they blend into the surrounding forest and wildflowers.
It’s easy to spend a day or two just unwinding and letting the day pass by - leisurely enjoying the facilities and walking around Prospect Berkshires’ beautiful grounds. They organize plenty of activities throughout the week including movie nights, water aerobics, tai chi, yoga and float therapy.
Prospect Berkshires have offered a discount code for our readers - use access code PARKSLOPE20 in the ‘Access Code’ field (not ‘Promo Code’) during booking for 20% off weeknight stays from Sept 1, 2026-Jan 30, 2027. Blackout dates apply; holidays excluded.
Where to Eat
The Cliff House
The Cliff House was a highlight of our stay. The food was bright, fresh and seasonal, and there’s a nice Brooklyn connection here too: the restaurant is now led by Polo Dobkin and Stephanie Lempert, the team behind Williamsburg’s Meadowsweet.
The Cliff House patio and dining room overlook Prospect Lake, where you can spot paddleboarders and kayakers on the water and watch the sunset over the mountains. There is both indoor and outdoor seating along with an intimate bar where you can enjoy creative twists on cocktails like the charred peach daiquiri.
The menu focuses on seasonal produce from local farms and producers. Start with snacks like pintxos or fish croquettes, or share some small plates like the heirloom tomato and watermelon salad (the sweetness was so memorable), along with their housemade cavatelli and corn. I also ordered the thick cut of heritage pork, caramelized in peach mostarda and complemented by corn grits. They were happy to accommodate our young kids by offering a simple pasta dish for them with butter and cheese.
The restaurant was a very convenient and elevated dining option for our family just a short walk from our cabin. The Cliff House is open daily for breakfast and dinner, with brunch offered on Sundays to both those visiting and guests at Prospect Berkshires. You can book your reservation on Resy here.
After dinner, the kids played on the swings and made s’mores with a complimentary kit at one of the nearby campfires. A few other guests joined us around the fire too, which made it a really nice way to end the evening.
A few more places to eat nearby
These local favorites - some recommendations from the Prospect Berkshires team (thank you!) - are also worth visiting:
The Prairie Whale: A classic, rustic, farm-to-table restaurant in Great Barrington serving a frequently changing menu built around locally sourced ingredients. The lively atmosphere, cocktails and seasonal American cooking have made it a longtime Berkshires favorite.
Hilltown Hot Pies: A recently opened brick-and-mortar restaurant in a historic restored farmhouse at Egremont (a 7-minute drive from Prospect Berkshires), focusing on naturally leavened, wood-fired sourdough pizza and Southern Italian cooking using ingredients from the Berkshires and New England. Reservations are recommended!
GB Eats in Great Barrington is a family-friendly diner offering all-day breakfast and comfort food - a relaxed, casual option with dishes for everyone to enjoy.
No Comply Foods: A casual Great Barrington eatery with a skater-punk vibe and a globally inspired menu that changes daily. There’s no alcohol, no tipping, no waitstaff and no reservations.
Things to do nearby
Bish Bash Falls is the highest single-drop waterfall in Massachusetts. Located in Mount Washington within Bash Bish Falls State Park, the water drops nearly 60 feet into a clear plunge pool, split into twin cascades by a large rock. There is a nice hike next to a stream from the New York side which is a 1.5 mile round trip (our 4 and 6 year olds last year were able to complete the hike with a rest at the waterfall). There are also limited parking spots closer to the falls.
Hancock Shaker Village is a history museum and working farm that preserves the legacy of the Shakers. There’s plenty to see and do for grown-ups and kids - featuring many historic buildings including a Round Stone Barn from the 1800s, daily craft demonstrations, farm animals and exhibits
Another museum worth a longer trip in the Berkshires is MASS MoCA, a contemporary art museum that is worth the 1 hour drive further north - and hours at its sprawling campus.
The museum is housed in a massive, restored 19th-century industrial factory campus in North Adams. They host many exhibitions at one time across over 25 buildings - I enjoyed Jeffrey Gibson’s POWER FULL BECAUSE WE’RE DIFFERENT’s colorful and loud exhibition celebrating queer and Indigenous communities - and Sol LeWitt: A Wall Drawing Retrospective (a long-term exhibition), spread over 3 floors in a historic mill building, each level contrasting different periods of his life across over 100 drawings.
They also have a Kidspace where kids can spend hours with special projects or use all sorts of materials for their own creations. The cafeteria was a convenient dining option with healthy options and a kids menu, while the $3 ice cream scoops were a welcome sight for the kids.
On the way up to MASS Moca we stopped by Windy Hill Farm to pick some blueberries - there was a beautiful nursery out front and we quickly filled pints of blueberries during our visit. There were also some apple trees and Christmas trees growing when we were there!
Google Map of the places in this guide
Thank you to Prospect Berkshires for the opportunity to stay, relax and enjoy the beautiful region! We can’t wait to be back again soon.