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Things To Do & Places To Go

Call or check websites to confirm days/hours of operation as some may have changed.


Roe Jan Brewing Co. in Hillsdale. Opened in 2020, a perfect destination for beer and food lovers alike.  This massive, beautifully restored facility features excellent food and a great select of beers, brewed on-site.  Can also get growlers to go.

Little Cat Lodge is a fantastic brand new restaurant and lodge located just two miles from TRF at the base of Catamount.  Opened by Noah Bernamoff, a James Beard award-nominated restaurateur, in 2022, this place is worth the hype!  

Cook & Larder offers prepared foods and pastries for take out or eat-in.  Located in the center of Hillsdale.

Zinnia's Dinnette, a fun, casual destination for an amazingly inventive menu (killer friend chicken) and a great vibe.

The Barn in South Egremont for dinner, great with or without kids.  Fantastic burgers and tacos. Live music most weekend nights.

Prairie Whale in Great Barrington.  Farm to table, great menu, outdoor seating. Good idea to make a reservation.

Bimi's Canteen in Chatham.  Great new restaurant getting rave reviews on charming Chatham Main Street.

Chatham Beer Farm / Yummy Kitchen / Greenhouse Cidery in Chatham.  The pop-up Yummy Kitchen is a great addition to this really fantastic spot.  Tons of seating both indoors and out.

North Star at The Alander Lodge in Copake.  Lovely restaurant and bar just 8 miles south of Hillsdale.

Stagecoach Tavern in Sheffield, MA, about 10 miles from the house.  Really old, funky tavern, part of Race Brook Lodge.  Great chef, fun to wander property after dinner. Music and events in barn some nights.  Appalachian Trail entrance on the grounds.

Copake General Store in Copake.  9am - 3pm only.  Excellent sandwiches to eat there on the porch, or pack for hiking.  Good specialty pantry staples here as well.

Old Mill in South Egremont.  Classic restaurant with a great menu.  Dining room or cozy tavern room.

Bazalion’s in Great Barrington.  If you are heading to GB for groceries, stop at this french cafe to pick up frozen (chocolate) croissants to prepare at home in the morning.  Excellent sandwiches, quiche, olive oil, pasta and supplies.

The Farmer’s Wife in Ancramdale.  Great for breakfast or lunch.

Lil Deb’s Oasis in Hudson, only open for dinner, casual, super friendly.  Inspired tropical/Latino.

Wm Farmer and Sons in Hudson, more upscale, beautiful room and food.  Make a reservation.

The Lantern Inn in Wassaic, NY.  A great stop if you are picking anyone up at the Metro North in Wassaic (closest Metro-North stop to the house, about a 30 min drive).

Catering / Private Chefs

The Farmer's Wife. Owners Emilie Sommerhoff and Job Yacubian do not disappoint!  This renowned catering company and store deliver top notch catering for all types of events.

Sylvia Becker.  Private chef with wide ranging menus inspired by international travel., 973-768-7313.  @she_cooks_she_travels

The Hudson Larder.  Chef Tehra Thorp is the founder of this catering and food services company.  In addition to personal chef services, they can also prepare pre-made meals available for purchase.


David Wurth.  Renowned owner of Hillsdale's beloved Crossroads.


Random Harvest.  Great menu of ready-made specialty foods. 518-325-9895

Farmers Markets

Hillsdale - Copake Farmers Market.  Roeliff Jansen Park just south of town on Route 22, Saturdays May through October, 9am to 1pm.  There are also well maintained walking trails around the park.

Great Barrington Farmers Market.  Every Saturday from Mother’s Day through October.

West Stockbridge Farmers Market.  Thursdays 3p - 6p May to early Oct

Chatham Farmers Market.  Fridays 3p - 7p, May to early Oct

Groceries & Fresh Food

Random Harvest.  Craryville.  Small but well curated grocery.  A worker-owned market, café and community space featuring food and goods sourced directly from farmers and producers. 


Big Y World Class Market.  Great Barrington.  Slightly higher-end large grocery store.


Guido’s Fresh Marketplace.  Great Barrington.  Higher-end meats, produce, prepared foods.


Hawthorne Valley Farm Store.  Harlemville.  This extension of the Hawthorne Valley Farm and Association is a health-conscious and earth-conscious destination for foodies from all over.    


IGA.  Hillsdale.  Basic but well stocked grocery just minutes from our farm.  Great meat department.

Pigasso Farm for incredible fresh meat.  Just south of Hillsdale in Copake, NY.


Roeliff Jansen Park is minutes away just south of town on Route 22 and is the perfect destination for short walks with open meadow views.  Easy trails no longer than 2.5 miles.


Harlem River Rail Trail. While there are still portions of this 46 mile trail that are under construction, there is a paved 1.3 mile section from Hillsdale heading south (with extension being added) and accessible behind Roe Jan Brewing Co in Hillsdale.  There is another beautiful, longer 3 mile stretch that begins at Orphan Farm Road (approximately 5 miles south of town on 22). Bikes and pets are allowed.


Appalachian Trail - A portion of the Appalachian Trail can be accessed near Taconic State Park.


Bash Bish Falls - The most dramatic and highest single drop waterfall in MA.  Bash Bish Falls Trail is a 2.1 mile out and back trail located near South Egremont, MA that features a waterfall and is good for all skill levels. 


Beebe Hill Fire Tower.  A 1.7 mile out and back trail near Austerlitz, NY, good for all skill levels. The trail is primarily used for hiking, walking, and mountain biking and is accessible year-round. Read more about the tower here.


Ooms Conservation Area at Sutherland Pond.  Conservation Area in Chatham features 2.9 miles of trails on 180 acres of land. This spectacular property includes rolling grasslands, pond, pastoral landscape.

Omi Sculpture Park. Non-profit arts center with a 120-acre sculpture and architecture park and gallery in Ghent, NY.  About a 25 min scenic drive. from the house.

Won Dharma Center.  7 miles of walking trails, free and open to the public from April to November.  12 miles west of Hillsdale on Rte 23.

Olivia's Overlook, Yokun Ridge South, Various hiking trails.  West Stockbridge, MA.

Take A Class

HGS Home Chef in Hillsdale, NY hosts frequent cooking classes for food-lovers of all levels. This large store features two beautiful teaching kitchens where renowned national and local experts offer classes on how to prepare the most delicious food — from simple to sublime.

Tiny Hearts Farm, a local organic flower grower, offers gardening and arranging workshops to the public through their Tiny Hearts Studio located right in Hillsdale. 

Workshop Experience Weekend.  This annual workshop festival features an array of workshops and garden tours in the Hillsdale area.  

Swimming Ponds

Green River Swimming Hole.  On Rte 23 towards Great Barrington.  “Walking the dirt path between the river to the west and the acres of corn fields to the east, it’s hard not to imagine an episode of the Andy Griffith Show playing out in this bucolic setting. Unlike rocky, mountainside swimming holes, this area of the Green River flows gently through farm fields and lowland forests.”  The Berkshires Blog

Direction: Driving along Route 23 heading towards Great Barrington, you will pass W.E.B. Du Bois National Historic Site, (612 S Egremont Rd, Great Barrington, MA 01230) on your left.  About .8 miles from there you will cross over the Green River. Immediately after the river, you will see corn fields. You can pull off and park there. From there, follow the path to the swimming hole.


Lake Taghkanic State Park.  Lake activities like fishing, boating & beach swims, plus hiking trails.  Great place for swimming with kids. Kayak and canoe rentals available.

Lake Mansfield.  This 29 acre pond is located very close to Great Barrington yet feels very secluded. Parking closeby and a small beach.  

Ore Pit Pond.  Part of Taconic State Park, Ore Pit Pond has a small swim area with a separate wading pool for young children.  

Guilder Pond.  Just west of Bash Bish in Mount Washington.


Rodger’s Book Barn.  Hillsdale.  Incredible used bookstore up a winding road west of town.  Really worth your time if you love bookstores jam packed with a carefully curated selection.  Owner Maureen Rodgers has been running the store for over 40 years and is a delight to chat with.  Large children’s section on the top floor for those with kids. 


Yellow House Books.  Great Barrington.  Wonderfully stocked and organized used bookstore. Fantastic sections on history, art, philosophy, and local subjects.  

Johnnycake Books is a bit farther away (located in Salisbury, CT, about a 25 minute drive) but, for those interested in rare and collectible books, is a fantastic place to spend a few hours.  Owner Dan Dyer is a wealth of information and a fantastic guide.

The Chatham Bookstore.  Chatham, NY

Oblong Books.  Millerton, NY

Movie Theaters & Drive Ins

The Triplex Cinema in Great Barrington is an excellent independent theater very close by.  


The Moviehouse, an independent theater showing a mix of blockbusters and independent films, is located in Millerton.    

Drive-in movie theater in Amenia, NY.  Charming, small drive-in movie theater with an amazing food/frozen custard stand, adjacent to the Four Brothers Pizza in Amenia, about a 30 minute drive from the house (also near Wassaic train stop).

The Crandell Theater in Chatham, NY.  Lovely old theater (with great popcorn!).  The oldest single screen movie theater in Columbia County.

Yoga & Meditation

Won Dharma Center is a Buddhist meditation center located near Claverack in a beautiful setting. In addition to free use of walking trails, they offer free meditation sessions, as well as donation-based yoga classes.

Greenhouse Yoga, Great Barrington

Bohdi Yoga & Spa, Hudson

Have An Adventure

Falconry Excursions.  Spend a few hours with Falconry Excursions stable of eagles, owls, falcons and hawks.  Goshen, NY


Explore the castle ruins of Bannerman Castle.  In a glorious state of decay on Pollepel Island, Bannerman can be toured in several ways: walking tours through the Bannerman Castle Trust, via passenger boat, and through kayak tours. See the website for all the details and individual tour websites.


See the Hudson River from a different perspective at Walkway Over the Hudson, which at 1.28 miles is the world’s longest elevated pedestrian walkway. It connects Dutchess and Ulster counties and their rail trails for hikers and bikers.  


Catamount Zip Tour & Aerial Adventure Park.  Glide over the Taconic mountains in the exciting new zipline at the newly renovated Catamount Mountain Resort.  Also, The Catamount Aerial Adventure Park is a must.  12 aerial trails, 180 challenge elements connected by various configurations of cable, wood, and rope form a unique, fun, challenging and rewarding experience in the trees. 


Adventure with Altitude Ballooning offers a number of trips to see the Hudson Valley from a uniquely quiet, majestic perspective.


Hudson-Athens Ferry.  Ferry trips from one great little town to another.  Multiple tours and trips available. 

Book a Private Tour.  Check out the many tours, day trips and adventures with  


Downhill Skiing: 

Catamount.  Catamount just had an extensive make-over and is proving to be a real ski destination.  Eight lifts and 42 varied trails, this is probably one of the best mid-sized ski resorts in New England.  Only two miles from the farm.  They also offer Snow-shoeing and cross country trails and rentals, as well as night skiing. 

Butternut.  A great family ski resort near Great Barrington for skiing, snowboarding and fun family activities like tubing.

Cross Country Skiing:

Art Omi.  Free of charge.  Explore the 2.5 miles of groomed trails in this sculpture and architecture park.  


Olana State Historic Site. There are 5 miles of carriage trails winding through this 250 acre property with fantastic views of the Hudson River and the Catskill Mountains.  The trails are free and open to the public.  

Copake Country Club. This public golf course offers all the necessary equipment for rent (skis, boots, poles, bindings). The cost is $25 if you rent their equipment, and just $10 to ski if you bring your own skis.

Nearby Towns To Explore

One of the things we love most about our part of New York is how many amazing small towns there are in such close proximity.  Here are a few:



Be sure to check out Hillsdale General Store, Cook & Larder, and C. Herrington for unique home good supplies and gifts.  Tiny Hearts Flower Shop is a lovely place to pick up flowers or arrangements.  


Great Barrington.

Really the gateway to the Berkshires, this small town has it all: large grocery stores, live performance theater, movie theater, great shopping, and fantastic restaurants.  A short 15 minute drive, Great Barrington is a great way to spend an afternoon or evening. The Mahaiwe historic theater right in the center of town offers a great lineup of music, dance, theater, opera, movies and family programming.  While several restaurants are listed above, there are a number of other notable restaurants including Baba Louie’s, Number 10, and The Bistro Box.  There are also some great antiquing destinations as well as homegoods and clothing shops including Hammertown and Karen Allen Fiber Arts.  


Great Barrington’s hipper cousin, Hudson is truly a unique food and shopping destination.  Conveniently located on the Amtrak Hudson line, the town is surrounded by Federal, Victorian and Queen Anne homes.  In the middle of it all is Warren Street which is chalk full of all sorts of stores and sights. The fantastic restaurants and stores are far too many to list in any comprehensive fashion -- see above for some of our favorites.  While Warren Street is lined with unique antique stores, don’t miss the slightly out of the way but massive Antique Warehouse. If you have a few extra hours for a short trip, check out Frederic Edwin Church’s home and property, Olana State Historic Site.  



The ever charming Chatham is a great place to spend a few hours.  Check out Bimi’s Cheese Shop to grab some staples or enjoy an amazing sandwich.  The nearby Chatham Brewing is an award-winning local craft brewery well worth the visit.  Other notable restaurants include Blue Plate and Our Daily Bread.  And the Chatham Bookstore is a nicely run community bookstore.



Millerton has charm to spare; small but packed with unique and unusual finds on every street.  It is the home to Harney & Sons tea company which offers factory tours as well as Irving Farm New York, which has recently moved it’s coffee roasting facilities into town.  You could say it’s a well caffeinated town. The Harlem Valley Rail Trail has trail access right in town and runs 10.6 miles through forests and pastures before reaching the Wassaic Amtrak station.  While Millerton does not have as many antique stores as Hudson, it does have some real gems including Millerton Antiques Center as well as Old Mill of Irondale.  Notable restaurants include 52 Main, The Millerton Inn, and Oakhurst DinerOblong Books is a well curated bookstore that’s worth the visit.

Lenox, MA.

Lenox is a beautiful resort town packed with places to shop and things to do.  Home of The Mount, Edith Wharton's home and gardens, as well as Tanglewood.  Located just 20 miles from Hillsdale.

Stockbridge, MA.

This small but scenic Berkshires town is home to the Norman Rockwell Museum.  Only 20 miles from Hillsdale.

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