Guidebook for Hillsdale
Food Scene
Hillsdale House
2634 New York 23Good family place for dinner as well as a bar.
Great family pizza restaurant and bar about 8 min drive from the house. Open late (for the area) if you get into town after 7pm.
12 locals recommend
Four Brothers
2828 NY-23Great family pizza restaurant and bar about 8 min drive from the house. Open late (for the area) if you get into town after 7pm.
Our favorite pizza restaurant. There is one in Hudson and in Great Barrington. I believe Great Barrington was the original though. Unique recipes. Voted #1 in Great Barrington by Trip Advisor - well deserved rating.
121 locals recommend
Baba Louie's Sourdough Pizza
42/44 Railroad StOur favorite pizza restaurant. There is one in Hudson and in Great Barrington. I believe Great Barrington was the original though. Unique recipes. Voted #1 in Great Barrington by Trip Advisor - well deserved rating.
Great restaurant for breakfast and lunch. This is an absolute must stop.
61 locals recommend
Crossroads Food Shop
2642 NY-23Great restaurant for breakfast and lunch. This is an absolute must stop.
Swiss Hutte
3290 MA-23Nice restaurant at the base of Catamount Ski area. (expensive)
Great restaurant - good for families as well - and part of the Copake Country Club. There is an amazing central fireplace in the winter. There is also a bar area for casual lunches if you're playing golf. Cross country skiing available in the winter too.
46 locals recommend
The Greens at Copake Country Club
44 Golf Course RdGreat restaurant - good for families as well - and part of the Copake Country Club. There is an amazing central fireplace in the winter. There is also a bar area for casual lunches if you're playing golf. Cross country skiing available in the winter too.
If you want meat, (to cook at home) this is where you go! This is also great for kids, there are chickens and pigs on the property and the chickens will come out to the parking lot.
9 locals recommend
Pigasso Farms
480 Farm RdIf you want meat, (to cook at home) this is where you go! This is also great for kids, there are chickens and pigs on the property and the chickens will come out to the parking lot.
John Andrews
224 Hillsdale RdOur favorite restaurant in the area.
Village Scoop Hand Crafted Ice Cream
2640 NY-23Amazing ice cream!
When you're done your hike at Bash Bish, or coming off the rail trail, stop here for their CinnaBombs cinnamon rolls - you won't (and will) regret it.
Depot Deli
64 Miles RdWhen you're done your hike at Bash Bish, or coming off the rail trail, stop here for their CinnaBombs cinnamon rolls - you won't (and will) regret it.
Locally sourced New American fare & regional wines in a laid-back space built from an old garage.
79 locals recommend
Local 111
111 Main StLocally sourced New American fare & regional wines in a laid-back space built from an old garage.
Cheery, rustic hangout pairs its solar-brewed beer with carefully sourced American comfort grub
51 locals recommend
Barrington Brewery & Restaurant
420 Stockbridge RoadCheery, rustic hangout pairs its solar-brewed beer with carefully sourced American comfort grub
Fun to go after a hike up to Bash Bish Falls or for drinks. They also have live music some nights.
10 locals recommend
Taconic Wayside Inn
108 NY-344Fun to go after a hike up to Bash Bish Falls or for drinks. They also have live music some nights.
Ca’Mea
214 Warren StVoted #1 restaurant in Hudson from Trip Advisor.
Voted #2 restaurant in Great Barrington by Trip Advisor.
55 locals recommend
Cafe Adam, Bar and Restaurant
420 Stockbridge RdVoted #2 restaurant in Great Barrington by Trip Advisor.
Solid, standard, inexpensive diner food at the intersection of 22 and 23. About a 5 min drive from the house.
11 locals recommend
O's Hillsdale Diner
9276 NY-22Solid, standard, inexpensive diner food at the intersection of 22 and 23. About a 5 min drive from the house.
Essentials
Hillsdale Supermarket
2628 NY-23Full grocery store.
Stewart's Shops
9248 NY-22Local convenience store and gas station - has great ice-cream!
CVS
362 Main StClosest drug store.
Biggest hospital in the area. 24 hour emergency room. About 30 min drive from the house.
14 locals recommend
Columbia Memorial Hospital
71 Prospect AveBiggest hospital in the area. 24 hour emergency room. About 30 min drive from the house.
Smaller hospital than in Hudson but a little bit closer to the house - about 20 min drive
8 locals recommend
Fairview Hospital
29 Lewis AveSmaller hospital than in Hudson but a little bit closer to the house - about 20 min drive
Local library. Nice quiet place to come an read, computers available as well as free wifi. Nice children's area as well.
6 locals recommend
Roeliff Jansen Community Library
9091 NY-22Local library. Nice quiet place to come an read, computers available as well as free wifi. Nice children's area as well.
Shopping
Berkshire Pottery
2891 NY-23Unique pottery made on premise. Great for gifts.
Hillsdale General Store
2642 NY-23Great gift store
Hillsdale Fine Wine & Spirits
8 Anthony StLocal wine store
Amazing gourmet market, they also sell wine because they are in MA. From their website: "Guido’s Fresh Marketplace has been the premier purveyor of quality produce in Berkshire County and neighboring areas."
248 locals recommend
Guido's Fresh Marketplace
760 S Main StAmazing gourmet market, they also sell wine because they are in MA. From their website: "Guido’s Fresh Marketplace has been the premier purveyor of quality produce in Berkshire County and neighboring areas."
Everything Else
United States Postal Service
9245 NY-22For all your postal needs
St Peters Catholic Church
213 Main StCatholic Church
We are a warm and welcoming community in the Berkshires of Western Massachusetts where people of many backgrounds and beliefs come together to worship and explore the richness of the Jewish tradition. Ahavath Sholom was founded in 1926 and is affiliated with the Jewish Reconstructionist Communities.
Ahavath Sholom Synagogue
15 North StWe are a warm and welcoming community in the Berkshires of Western Massachusetts where people of many backgrounds and beliefs come together to worship and explore the richness of the Jewish tradition. Ahavath Sholom was founded in 1926 and is affiliated with the Jewish Reconstructionist Communities.
Entertainment & Activities
Family friendly ski area, 10 minute drive! They also have night skiing and a ropes course in the summer.
329 locals recommend
Catamount Mountain Ski Resort
78 Catamount RdFamily friendly ski area, 10 minute drive! They also have night skiing and a ropes course in the summer.
Great Barrington is about a 25min drive from the house and has an abundance of restaurants and shopping
188 locals recommend
Great Barrington
Great Barrington is about a 25min drive from the house and has an abundance of restaurants and shopping
Historic town with lots of great restaurants, antique shops, and specialty shops. About a 25-30min drive.
442 locals recommend
Hudson
Historic town with lots of great restaurants, antique shops, and specialty shops. About a 25-30min drive.
Fairview Cinema III
160 Fairview AveThe Triplex Cinema
70 Railroad StTwo sections totaling 15 paved miles through stunning rural Dutchess and Columbia County landscapes
6 locals recommend
Harlem Valley Rail Trail
Harlem Valley Rail TrailTwo sections totaling 15 paved miles through stunning rural Dutchess and Columbia County landscapes
Taconic State Park
253 NY-344Swimming hole - great for hot days in the summer.
Jiminy Peak
37 Corey RdNice family friendly skiing within a 45 min drive.
Apple picking in the fall as well as year round wine tasting. THE BEST apple cider doughnuts I have ever eaten.
27 locals recommend
Bartlett's Orchard
575 Swamp RdApple picking in the fall as well as year round wine tasting. THE BEST apple cider doughnuts I have ever eaten.
Great pick-your-own fruits and vegetables. Blueberries, strawberries, apples, cherries, broccoli and more.
29 locals recommend
Samascott Orchards
5 Sunset AveGreat pick-your-own fruits and vegetables. Blueberries, strawberries, apples, cherries, broccoli and more.
Small, family oriented ski area. Great for beginners. They also have a super fun snow tubing hill - fun for everybody.
218 locals recommend
Ski Butternut
380 State RdSmall, family oriented ski area. Great for beginners. They also have a super fun snow tubing hill - fun for everybody.
Parks & Nature
Hiking, cycling, climbing. There are easy hiking trails up to the falls as well as a few more challenging options. Great for families. This is a really nice hike when it's not too busy. You can walk from the bottom up, or from the top down - two parking options. Coming from the top can be steep for some people. There is also a roundabout hike starting from the lower lot that is about 3 miles round trip and more challenging (that loop is not recommended for small children)
282 locals recommend
Bash Bish Falls State Park
Falls RoadHiking, cycling, climbing. There are easy hiking trails up to the falls as well as a few more challenging options. Great for families. This is a really nice hike when it's not too busy. You can walk from the bottom up, or from the top down - two parking options. Coming from the top can be steep for some people. There is also a roundabout hike starting from the lower lot that is about 3 miles round trip and more challenging (that loop is not recommended for small children)
Ascend this popular peak, which once drew 19th-century literary giants, and from its summit gaze across the spectacular landscapes of the Housatonic River Valley.
112 locals recommend
Monument Mountain Reservation
Ascend this popular peak, which once drew 19th-century literary giants, and from its summit gaze across the spectacular landscapes of the Housatonic River Valley.
A few great hiking trails and a Appalachian Trail intersection with a great view at the top. Rough, gravel road up to the upper parking area.
11 locals recommend
Mount Everett State Reservation
143 East StreetA few great hiking trails and a Appalachian Trail intersection with a great view at the top. Rough, gravel road up to the upper parking area.
You’re in the mood for a stroll and you appreciate a big fat waterfall.
128 locals recommend
High Falls Conservation Area
540 Roxbury Rd You’re in the mood for a stroll and you appreciate a big fat waterfall.
A series of wel.-marked hiking trails snake through some strikingly massive and odd-looking stones, many of them topped with moss
45 locals recommend
Bartholomew's Cobble Reservation
105 Weatogue RdA series of wel.-marked hiking trails snake through some strikingly massive and odd-looking stones, many of them topped with moss
Very nice hiking - you probably won't see another person the entire time! One section of tall grass though, be prepared with but/tick repellant.
http://berkshirehiking.com/hikes/jug_end.html
9 locals recommend
Jug End
Very nice hiking - you probably won't see another person the entire time! One section of tall grass though, be prepared with but/tick repellant.
http://berkshirehiking.com/hikes/jug_end.html
Arts & Culture
Lots of summer music festivals and performers. Only about a 35 min drive.
15 locals recommend
Tanglewood Lions Gate
Hawthorne RoadLots of summer music festivals and performers. Only about a 35 min drive.
Norman Rockwell Museum
9 Glendale RdGreat Norman Rockwell collection and museum
Olana State Historic Site was the home of Frederic Edwin Church, one of the major figures in the Hudson River School of landscape painting.
350 locals recommend
Olana State Historic Site
Olana State Historic SiteOlana State Historic Site was the home of Frederic Edwin Church, one of the major figures in the Hudson River School of landscape painting.
Berkshire Museum
39 South StSurprisingly nice museum. Great for kids.
Massachusetts Museum of Contemporary Art just a little over an hour drive away.
382 locals recommend
MASS MoCA
1040 Mass MoCA WayMassachusetts Museum of Contemporary Art just a little over an hour drive away.