Berkshire Guidebook
Hiking
Great moderate hike, about 30 minutes. Steep at top.
112 locals recommend
Monument Mountain Reservation
Great moderate hike, about 30 minutes. Steep at top.
Lots of hikes and natural elements - Sages Ravine, Guilder Pond, Appalachian Trail, Alander Mountain, and many more trails.
15 locals recommend
Mount Washington State Forest
143 East StreetLots of hikes and natural elements - Sages Ravine, Guilder Pond, Appalachian Trail, Alander Mountain, and many more trails.
Tallest mountain in Massachusetts. Long day. Can also drive up.
39 locals recommend
Mount Greylock State Reservation Visitor Center
30 Rockwell RdTallest mountain in Massachusetts. Long day. Can also drive up.
Three minutes from the house. Gorgeous walk down to the Green River. Great swimming for everyone. Park on Haley Road.
McCallister Park
Three minutes from the house. Gorgeous walk down to the Green River. Great swimming for everyone. Park on Haley Road.
Five minutes from the house. Twenty minute flat loop along the Housatonic River. Great for kids.
8 locals recommend
Housatonic Flats Reserve
439 Stockbridge RdFive minutes from the house. Twenty minute flat loop along the Housatonic River. Great for kids.
Gorgeous Trails. Flat. Great for kids. Sheffield - ten minutes away.
45 locals recommend
Bartholomew's Cobble Reservation
105 Weatogue RdGorgeous Trails. Flat. Great for kids. Sheffield - ten minutes away.
Small flat walk through covered bridge and an old farm road. Twenty minute walk. Where the UFO landed .... look that one up.
Upper Sheffield Bridge
Small flat walk through covered bridge and an old farm road. Twenty minute walk. Where the UFO landed .... look that one up.
You can hop on the Appalachian Trail in many spots in Great Barrington, Sheffield and other Berkshire spots.
Appalachian Trail
Appalachian National Scenic TrailYou can hop on the Appalachian Trail in many spots in Great Barrington, Sheffield and other Berkshire spots.
Tyringham Cobble Park
20 Jerusalem RdGreat hike. Fifteen minutes away.
Neighborhoods
Railroad Street
Railroad StreetA few blocks away...restaurants, SoCo Ice Cream, coffee shops and other shops.
City/town information
Small Farm Town. South of Great Barrington. Market Place. Pizza Shop and New bakery. Brewery. Lots of farm roads to explore.
11 locals recommend
Sheffield
Small Farm Town. South of Great Barrington. Market Place. Pizza Shop and New bakery. Brewery. Lots of farm roads to explore.
Home of Norman Rockwell and the museum. Have a cocktail on the porch of the historic Red Lion Inn. Walk around the town - bakery, coffee shop and other great little shops.
69 locals recommend
Stockbridge
Home of Norman Rockwell and the museum. Have a cocktail on the porch of the historic Red Lion Inn. Walk around the town - bakery, coffee shop and other great little shops.
Traveler advice
Customs and culture
Be Kind
The town is used to lots of visitors year round. Have fun. Welcome to the Berkshires.