36 East Guide
Skiing and Snowboarding
Bousquet Ski Area
101 Dan Fox DrSki Butternut
380 State RdCatamount Mountain Ski Resort
78 Catamount RdJiminy Peak
37 Corey RdHiking
This hike is approximately 20 minutes away, past Seekonk Tree Farm in Great Barrington. There are two different loop hikes, somewhat of a challenge but worth it for the different scenery and views.
8 locals recommend
Alford Springs
2-20 Old Village RdThis hike is approximately 20 minutes away, past Seekonk Tree Farm in Great Barrington. There are two different loop hikes, somewhat of a challenge but worth it for the different scenery and views.
This hike can be packed on weekends, but the views from the top are wonderful, so it's no wonder why.
53 locals recommend
Monument Mountain
This hike can be packed on weekends, but the views from the top are wonderful, so it's no wonder why.
A quieter, more gentle hike, this trailhead is located just down the road from Monument Mountain on Route 7.
Fountain Pond State Park
U.S. 7A quieter, more gentle hike, this trailhead is located just down the road from Monument Mountain on Route 7.
With trails on both sides of the road, this trailhead is lots of options. The parking lot is on the small side, so arrive early if you can!
51 locals recommend
Olivia's Overlook
Hiking TrailsWith trails on both sides of the road, this trailhead is lots of options. The parking lot is on the small side, so arrive early if you can!
Down the road from Olivia's Overlook, it's a peaceful hike to a beautiful waterfall.
17 locals recommend
Stevens Glen Trail Head Richmond, MA
Lenox RoadDown the road from Olivia's Overlook, it's a peaceful hike to a beautiful waterfall.
There are endless loops you can create from the trailhead behind the Arcadian Shop. Look at the map online or get one in the cafe before hitting the trails. There are maps spread throughout the place but I've gotten myself "lost" in some far back corners of the park by exploring too much, if that's possible. This is an absolute go to for us since it's less than 10 minutes away.
Kennedy Park - Access
91 Pittsfield RdThere are endless loops you can create from the trailhead behind the Arcadian Shop. Look at the map online or get one in the cafe before hitting the trails. There are maps spread throughout the place but I've gotten myself "lost" in some far back corners of the park by exploring too much, if that's possible. This is an absolute go to for us since it's less than 10 minutes away.
There is an access point by the old train station in Lenox Dale. From there, cross the bridge from the track and walk the dirt road and you'll end up in the state park. Look at the map online, there's a trail that goes up a brook to a reservoir and it's pretty challenging all up hill but really pretty. You can also access the state park by the October Mountain Campground in Lee.
33 locals recommend
October Mountain State Forest
317 Woodland RoadThere is an access point by the old train station in Lenox Dale. From there, cross the bridge from the track and walk the dirt road and you'll end up in the state park. Look at the map online, there's a trail that goes up a brook to a reservoir and it's pretty challenging all up hill but really pretty. You can also access the state park by the October Mountain Campground in Lee.
This is an easy loop hike that joins up with the Appalachian Trail for a short while. There is a small beach located at the state park as well.
20 locals recommend
Benedict Pond Loop
This is an easy loop hike that joins up with the Appalachian Trail for a short while. There is a small beach located at the state park as well.
Basin Pond
4-22 Becket RdGood loop hike with an arm trail that leads to the pond. Very peaceful!
For both hiking and kayaking, Upper Goose Pond is glorious. Parking is on right of Route 20 headed through Becket. It is Appalachian Trail parking. It walks over the Mass Pike. Approximately 6 miles round trip to the cabin and back.
Upper Goose Pond
For both hiking and kayaking, Upper Goose Pond is glorious. Parking is on right of Route 20 headed through Becket. It is Appalachian Trail parking. It walks over the Mass Pike. Approximately 6 miles round trip to the cabin and back.
Half of this trail leads along the Appalachian Trail. It's just 2.4 miles round trip and leads to great views on top. The field portion can be overrun with poisonous parsnip during the summer, so steer clear of those pretty yellow blossoms!
19 locals recommend
Tyringham Cobble Park
20 Jerusalem RdHalf of this trail leads along the Appalachian Trail. It's just 2.4 miles round trip and leads to great views on top. The field portion can be overrun with poisonous parsnip during the summer, so steer clear of those pretty yellow blossoms!
Kayaking
Take the first right after the Lee Premium Outlets to lead down the road to the boat launch at Lower Goose Pond. Strenuous against the wind, but well worth it, take the outlet on the other side of the pond to get to Upper Goose Pond, the Appalachian Trail cabin, and the little island in the middle perfect for a picnic!
Goose Pond
Take the first right after the Lee Premium Outlets to lead down the road to the boat launch at Lower Goose Pond. Strenuous against the wind, but well worth it, take the outlet on the other side of the pond to get to Upper Goose Pond, the Appalachian Trail cabin, and the little island in the middle perfect for a picnic!
Launch from the boat launch on Route 183. If you follow the lake along the right shoreline, it'll lead into a quiet section that breaks off the lake. There's a wonderful island in the middle of the lake, too, that has a couple picnic tables for relaxing!
20 locals recommend
Stockbridge Bowl
Launch from the boat launch on Route 183. If you follow the lake along the right shoreline, it'll lead into a quiet section that breaks off the lake. There's a wonderful island in the middle of the lake, too, that has a couple picnic tables for relaxing!
Groceries
Guido's Fresh Marketplace
760 S Main StGuido's Fresh Marketplace
760 S Main StBig Y World Class Market
10 Pleasant StPrice Chopper
Apple Orchards
Bartlett's Orchard
575 Swamp RdHilltop Orchards Home of Furnace Brook Winery
508 Canaan RdWindy Hill Farm
686 Stockbridge RdWine and Beer
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdLes Trois Emme Vineyard & Winery
8 Knight RdBright Ideas Brewing
111 Mass MoCA WayBalderdash Cellars
81 State RdBerkshire Mountain Distillers
356 S Main StBig Elm Brewing
65 Silver StNejaime's Wine Cellar
3 Elm StShopping
Famous for their vanilla extract, but a store filled with delicious, interesting and fun items for the whole family.
6 locals recommend
Charles H. Baldwin & Sons
1 Center StFamous for their vanilla extract, but a store filled with delicious, interesting and fun items for the whole family.
Sidetracks
8 Elm StOzzie's Glass Gallery
1670 Pleasant StWindy Hill Farm
686 Stockbridge RdWilliams & Sons Country Store
38 Main StPeace Love & Chocolate
36 Main StDesign Menagerie
26 Housatonic StArcadian Shop
91 Pittsfield RdTom's Toys
297 Main StMatrushka Toys & Gifts
309 Main St