Top 10 Things to do in Sheffield, United States

February 1, 2018 Hana Mouser

Sheffield is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. The population was 3,257 at the 2010 census. Sheffield is home to Berkshire School, a private preparatory school. The former resort town includes the village of Ashley Falls, and is bordered by various other towns and villages, such as Egremont and Great Barrington.
Restaurants in Sheffield

1. Catamount Ski Area

Route 23, South Egremont, MA +1 800-342-1840
Excellent
37%
Good
47%
Satisfactory
14%
Poor
1%
Terrible
1%
Overall Ratings

4 based on 62 reviews

Catamount Ski Area

Located on the border of Massachusetts and New York State, ski area offers trails on both the Berkshire Mountains and the Taconic Range.

Reviewed By BuffaloBird - Buffalo

We visited Catamount for the first time for a family ski day. Conditions were good. Location was beautiful. The first trail we took was the ridge trail- a green. We didn’t like how narrow and sloped it was. Difficult terrain for our youngest skier. Wouldn’t recommend for a beginner. Overall we had a good day. Things do feel a bit dated though. Not sure we would return.

2. Monument Mountain

Route 7, Great Barrington, MA 01230 +1 978-921-1944
Excellent
65%
Good
31%
Satisfactory
3%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 230 reviews

Monument Mountain

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.

Reviewed By philipu2015 - Bedminster

A gem no doubt, I recommend this hike for just about everyone except those on wheelchairs. With something for everyone, there is an easy route a moderate route with a hike along the top that will get your heart pumping. It was packed on Saturday so come early. Hint: pay for parking before you go - I missed it completely and found a note on my car gently reminding me of my financial obligation to pay- nice touch. I promptly and happily paid my 5 bucks at the kiosk. With the fall foliage, you’d have an even better experience if you go now, but would be a great hike anytime.

3. Catamount Aerial Adventure Park

3200 State Route 23, Hillsdale, NY 12529-5803 +1 518-325-3200
Excellent
78%
Good
19%
Satisfactory
0%
Poor
0%
Terrible
3%
Overall Ratings

4.5 based on 76 reviews

Catamount Aerial Adventure Park

Reviewed By Nelly G

I zip lined once in Costa Rica but this place was so much more than just zip lining. We had a large group of about 15+ I think and this place was great for everyone. No matter if you've had any experienced or level. Definitely challenges you. There's a great area to sit and relax and catch your breathe and hydrate. It was a very hot day, I would say it was in the high 80s/low 90s but under the trees you definitely didn't feel it.
Definitely want to go back there again. Highly recommend it.

4. Les Trois Emme Winery

8 Knight Rd, New Marlborough, MA 01230-1495 +1 413-528-1015
Excellent
70%
Good
30%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 30 reviews

Les Trois Emme Winery

Reviewed By cwmass - Prospect, Connecticut

Les Trois Emme winery is owned by the sweetest couple - Mary Jane & Wayne who treat everyone like family! We make the trip up from Connecticut every time they have their blues guitar player Bruce Gregori there - he's great! We love their Shiraz-Cabernet blend and their appetizers they give you with your tasting are delicious! We've been to a lot of wineries, and this is by far our favorite!

Claudia & Buck, CT

5. Berkshire Mountain Distillers

356 S Main St, Sheffield, MA 01257-9676 +1 413-229-0219
Excellent
79%
Good
19%
Satisfactory
2%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 42 reviews

Berkshire Mountain Distillers

Reviewed By Christine F

Good local spot to taste and purchase locally distilled spirits like gin, vodka, and some young bourbons aged in a variety of barrels (scotch and assorted beers) imparting different flavors. Didn't stay for the tour, however, did appreciate the opportunity to taste several varieties before...MoreChristine, Thanks for your review! Glad you liked our Berkshire Bourbon. One correction, our bourbon is not blended with rye but rye is in the mash bill in the Berkshire bourbon. Hope to see you again soon!

6. Ski Butternut

380 State Rd, Great Barrington, MA 01230-1463 +1 413-528-2000
Excellent
44%
Good
37%
Satisfactory
15%
Poor
2%
Terrible
2%
Overall Ratings

4 based on 199 reviews

Ski Butternut

Reviewed By diasmaribela

I love the variety of runs there are! I’ve been coming to butternut since i was very little and i still have the same excitement every time! Most blacks are relatively easy and the terrain parks are nice. definitely recommend!

7. Bartholomew's Cobble

105 Weatogue Rd, Sheffield, MA 01257-9012 +1 413-229-8600
Excellent
71%
Good
27%
Satisfactory
0%
Poor
2%
Terrible
0%
Overall Ratings

4.5 based on 36 reviews

Bartholomew's Cobble

Created by geologic upheavals a half-billion years ago, this hundred-foot-high bedrock outcropping introduces visitors to a rugged and exotic landscape that also supports 800 species of plants while offering terrific mountain vistas.

Reviewed By murrayhiller - murrayhill

A remarkable enclave combining great natural beauty, traditional farming and cultivation, and historical preservation. An hours walk here is a shortcut to the essence of the Berkshire with its mix of riverbed, wide valleys, rocky cobbles, and views of high hills. The Spero loop is especially noteworthy as is the vista from the high meadow to Mt Everett. Nice visitors center too.

8. Umapchene Falls Park

Umapchene Falls Rd, New Marlborough, MA
Excellent
50%
Good
50%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 8 reviews

Umapchene Falls Park

Reviewed By Darlene K - Hamburg, New York

We heard a lot about the falls at Umpachene Park and decided to take the drive. Driving close to our destination, we found detour signs that the bridge was closed. Even though we followed the detour signs, we kept going in circles. We came across some folks walking and they directed us on how to get there. Glad we asked. A short very easy walk for a really pretty view of the falls. This particular falls is wider than other falls in the area, nice cascading waters. There were several people either in the water, sunbathing on the rocks or just sitting enjoying the day. Nice local casual hang out on a sunny day.

9. Beartown State Forest

69 Blue Hill Rd, Monterey, MA +1 413-528-0904
Excellent
37%
Good
53%
Satisfactory
5%
Poor
5%
Terrible
0%
Overall Ratings

4 based on 37 reviews

Beartown State Forest

Reviewed By EcoM8s - Great Barrington, Massachusetts

There's just something about the woods in winter and ice on a pond! This is such a beautiful walk/hike around the pond; about 2 miles. It's relatively flat so an easy/moderate walk and good for dogs. In the winter you will need sturdy boots with spikes and/or traction cleats (such as Yaktrax); especially if there has been a thaw/freeze cycle. Today there were a few people out ice fishing. On chilly winter days bring some hot beverages and enjoy overlooking the pond from picnic tables.

10. Kenver LTD.

39 Main St, South Egremont, MA 01258-9717 +1 413-528-2330
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 3 reviews

Kenver LTD.

Kenver is a family owned outdoor recreation store dedicated to adventure, fashion and excellence. The building, built in 1731, maintains a historic ambiance with fireplaces and antiques throughout. Our knowledgeable staff is always excited to help find what you need to enjoy the beauty of the Berkshires and beyond. We invite you to come see for yourself why shopping at Kenver a real experience!

Reviewed By Redmcx - Hartford, CT

I recently purchased a pair of boutique ski boots from Kenver. My customer experience was superior in every regard. I've been skiing at a high level since I was a kid and worked as a ski tech for a couple of seasons, so I probably present as the prototypical nightmare consumer; i.e. one who will spend money on performance gear but only after copious research, slowly driving the sales staff insane; and only then, grudgingly, whipping out the credit card. No worries on this score for Aaron at Kenver, an excellent dude who helped me understand the product, looked into options, gave me downtime to stew over my decisions and then had the connections to find me the boots for a fair price. He efficiently handled the in-store fitting process and then personally adjusted the bindings while I waited. Can you possibly go wrong with that level of attention to detail? Answer: only if you secretly don't think you're worth it. But you are.

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