Jim & Phoebe’s Guide to Hikes and other Activities
Museums
A small museum highlighting Litchfield's historic past
14 locals recommend
Litchfield Historical Society
7 South StA small museum highlighting Litchfield's historic past
Part of the Litchfield Historical Society's offerings
16 locals recommend
Tapping Reeve House and Law School
82 South StPart of the Litchfield Historical Society's offerings
An outstanding collection of American clocks and timepieces, showcasing Connecticut's contribution to American manufacturing.
7 locals recommend
American Clock & Watch Museum
100 Maple StAn outstanding collection of American clocks and timepieces, showcasing Connecticut's contribution to American manufacturing.
A fascinating collection of Merry-go-round artifacts from America's bygone era of amusement parks.
12 locals recommend
New England Carousel Museum
95 Riverside AveA fascinating collection of Merry-go-round artifacts from America's bygone era of amusement parks.
More interesting than the name would suggest, this museum was founded by Winsted native Ralph Nader.
The American Museum of Tort Law
654 Main StMore interesting than the name would suggest, this museum was founded by Winsted native Ralph Nader.
An extraordinary collection of early American tools.
12 locals recommend
Eric Sloane Museum & Kent Furnace
31 Kent Cornwall RdAn extraordinary collection of early American tools.
An excellent art and history museum showcasing the Naugatuck Valley.
19 locals recommend
Mattatuck Museum
144 W Main StAn excellent art and history museum showcasing the Naugatuck Valley.
The best collection of Impressionist Paintings in Connecticut in a gorgeous setting.
18 locals recommend
Hill-Stead Museum
35 Mountain RdThe best collection of Impressionist Paintings in Connecticut in a gorgeous setting.
White Memorial Conservation Center
80 Whitehall RdA small museum all about nature.
Our favorite hikes
Some of the nicest hiking in the county is right around the corner. Make sure to use bug spray or you might be frustrated by the little monsters.
Less than a mile round trip, this short hike down the road to the waterfall and swimming hole is a must for our guests.
Perkins Road
Perkins RoadLess than a mile round trip, this short hike down the road to the waterfall and swimming hole is a must for our guests.
The land trust owns several properties with trails. Our favorites are the Upper Bantam River Trail (381 Torrington Road), The Stillman-Danaher Trail (Now accessible from Perkins Road), and the Prospect Mountain Trail (Cathole Road in Bantam)
Litchfield Land Trust
28 Bantam RdThe land trust owns several properties with trails. Our favorites are the Upper Bantam River Trail (381 Torrington Road), The Stillman-Danaher Trail (Now accessible from Perkins Road), and the Prospect Mountain Trail (Cathole Road in Bantam)
A beautiful setting with short hikes and a stunning Tudor house
31 locals recommend
Topsmead State Forest
A beautiful setting with short hikes and a stunning Tudor house
Miles of trails. Some of the trails might be crowded on nice weekends but there are plenty of out of the way trails that you can have almost to yourself. The boardwalk around little pond is a must. Bring bug spray.
71 locals recommend
White Memorial Conservation Center
80 Whitehall RdMiles of trails. Some of the trails might be crowded on nice weekends but there are plenty of out of the way trails that you can have almost to yourself. The boardwalk around little pond is a must. Bring bug spray.
This trail is part of the extensive Mattatuck trail that traverses the county. The Leatherman was reported to have used the cave as part of his annual trek.
6 locals recommend
Leatherman's Cave
This trail is part of the extensive Mattatuck trail that traverses the county. The Leatherman was reported to have used the cave as part of his annual trek.
In addition to swimming and picnicking, Mt Tom offers some excellent hiking trails. The tower trail is a favorite. The stone tower at the summit offers 360 degree views of the county. On a clear day, you can see New York and Massachusetts.
44 locals recommend
Mount Tom State Park
Mount Tom RoadIn addition to swimming and picnicking, Mt Tom offers some excellent hiking trails. The tower trail is a favorite. The stone tower at the summit offers 360 degree views of the county. On a clear day, you can see New York and Massachusetts.
Like Mt Tom, Haystack offers an impressive stone tower at the summit.
11 locals recommend
Haystack Mountain Tower
Like Mt Tom, Haystack offers an impressive stone tower at the summit.
For a more rigorous hike, the Appalachian Trail passes over the summit of Bear Mountain. You can hike up to the summit from the south side, and then descend down the steeper north side and loop back to the access trail. We also like taking a backpack, climbing over the summit and then camping out in Sages Ravine or Race Mountain. Then the next day going over the top of Race Mountain and down the Race Brook Falls Trail to the road. It requires taking two cars or leaving a bicycle at the Race Brook trailhead, but it is well worth it.
19 locals recommend
Bear Mountain
For a more rigorous hike, the Appalachian Trail passes over the summit of Bear Mountain. You can hike up to the summit from the south side, and then descend down the steeper north side and loop back to the access trail. We also like taking a backpack, climbing over the summit and then camping out in Sages Ravine or Race Mountain. Then the next day going over the top of Race Mountain and down the Race Brook Falls Trail to the road. It requires taking two cars or leaving a bicycle at the Race Brook trailhead, but it is well worth it.
A fairly easy hike to one of the nicest waterfalls in western Massachusetts.
282 locals recommend
Bash Bish Falls State Park
Falls RoadA fairly easy hike to one of the nicest waterfalls in western Massachusetts.
There are two falls here, the upper and the lower, both of which are beautiful, especially in the spring or after a rainy spell. The lower falls is an easier hike, but for the more energetic, I recommend the upper.
22 locals recommend
Race Brook Falls
There are two falls here, the upper and the lower, both of which are beautiful, especially in the spring or after a rainy spell. The lower falls is an easier hike, but for the more energetic, I recommend the upper.
A lovely park with spectacular falls, the trail takes you up to the top of the falls and back down the other side. Picnic tables abound here so make a day of it.
121 locals recommend
Kent Falls State Park
462 Kent Cornwall RdA lovely park with spectacular falls, the trail takes you up to the top of the falls and back down the other side. Picnic tables abound here so make a day of it.
Beautiful State Park in New Preston. hiking, swimming, and boating.
29 locals recommend
Lake Waramaug State Park
30 Lake Waramaug RdBeautiful State Park in New Preston. hiking, swimming, and boating.
Steep Rock Preserve
2 Tunnel RdSpectacular views, really cool old train tunnel.
Bike Paths and Rail Trails
These are some of the nicest bike trails around. If you are more of a road biker, just ask Jim to recommend roads for all day bicycling.
A very well maintained cinder and gravel bike/hike trail connecting Litchfield and Bantam
Litchfield Community Greenway Trailhead on South Lake Street
South Lake StreetA very well maintained cinder and gravel bike/hike trail connecting Litchfield and Bantam
A very nice asphalt bike path that goes almost from Torrington to Winsted.
Sue Grossman Still River Greenway
18 Lanson DrA very nice asphalt bike path that goes almost from Torrington to Winsted.
This extensive trail system goes from New Haven, CT up to Westfiield, MA. It can be crowded in some spots, especially when the weather is nice, but if you go north of Simsbury, you will have plenty of trail to yourself.
14 locals recommend
Farmington Canal Heritage Trail
480 Cornwall AveThis extensive trail system goes from New Haven, CT up to Westfiield, MA. It can be crowded in some spots, especially when the weather is nice, but if you go north of Simsbury, you will have plenty of trail to yourself.
Make a day of it and ride this lovely bike path with spectacular views of the Berkshires.
74 locals recommend
Ashuwillticook Rail Trail
Rail TrailMake a day of it and ride this lovely bike path with spectacular views of the Berkshires.
This is a gem of a bike path that goes from Wassaic to Copake Falls.
19 locals recommend
Harlem Valley Rail Trail
Harlem Valley Rail TrailThis is a gem of a bike path that goes from Wassaic to Copake Falls.
Water Activities
Canoe and Kayak Rentals. We highly recommend taking a boat out on the Bantam River from Alain White Road.
Sportsmen's of Litchfield
725 Bantam RdCanoe and Kayak Rentals. We highly recommend taking a boat out on the Bantam River from Alain White Road.
Rent a Kayak, Canoe, or Tube and ride on the Farmington River.
38 locals recommend
Collinsville Canoe & Kayak
41 Bridge StRent a Kayak, Canoe, or Tube and ride on the Farmington River.
Mount Tom State Park
Mount Tom RoadCool water for swimming.
Clarke Outdoors
163 US-7Kayak and Canoe rentals on the housatonic
Mini Golf
Matterhorn Mini Golf
10 Dyer Cemetery Rd
Riverfront Miniature Golf
218 River RdOne of our favorites with the kids.
A fun mini golf and ice cream spot - they also have a driving range.
7 locals recommend
Farmington Miniature Golf & Ice Cream
1048 Farmington AveA fun mini golf and ice cream spot - they also have a driving range.
R&B Sports World
19 Rowley StMini golf, go carts and batting cages.
Norbrook Farm Disc Golf Course
204 Stillman Hill RoadEnjoy a brew and try the three mile disc golf course.
Sightseeing
Guided horseback riding on nice trails through Topsmeade State Forest
14 locals recommend
Lee's Riding Stable
57 E Litchfield RdGuided horseback riding on nice trails through Topsmeade State Forest
Wineries, distilleries, breweries
Sunset Meadow Vineyards
599 Old Middle StKent Falls Brewing
33 Camps RdBerkshire Mountain Distillers
356 S Main StVery good Bourbon and gin.
Bad Dog Brewing Company
117 Water StreetA cool place in the old Torrington Fire Co. building.
Brewery Legitimus
283 Main St
Brass Works Brewing Company
2066 Thomaston AveVery good brews.
Little Red Barn Brewers
32 Lake StThis place has become the go to place for hard cider tasting on weekends. If the weather is nice you might have trouble finding a place to park.
7 locals recommend
Hogan's Cider Mill
522 Spielman HwyThis place has become the go to place for hard cider tasting on weekends. If the weather is nice you might have trouble finding a place to park.
haven't been there in a while, but the last time I was there, the wine was very good.
50 locals recommend
Hopkins Vineyard
25 Hopkins Roadhaven't been there in a while, but the last time I was there, the wine was very good.
Evening Sky Brewing Company
280 Spielman HighwayThis brewery is only about 20 minutes away. Excellent brews!
Good bourbon, good gin. A nice place to visit. about 45 minutes away.
35 locals recommend
Berkshire Mountain Distillers
356 S Main StGood bourbon, good gin. A nice place to visit. about 45 minutes away.
Norbrook Farm Brewery
204 Stillman Hill Rd