Windsor, Connecticut
Top Spots in and near Windsor
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Great Barrington, Massachusetts
Mt. Wilcox and Beartown Mountain Trail Loop
5.09.29 mi / 981 ft gainMt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.Read more -
Salisbury, Connecticut
Bear Mountain Loop
4.56.05 mi / 1516 ft gainAt 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...Read more -
East Lyme, Connecticut
Hike Rocky Neck State Park Trail
5.02.5 mi / 141 ft gainRocky Neck State Park Trail is a 2.5 mile loop hike where you may see beautiful wild flowers located near East Lyme, Connecticut.Read more -
Deerfield, Massachusetts
South Sugarloaf Trail
1.48 mi / 404 ft gainSouth Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.Read more -
Sheffield, Massachusetts
Hike to Race Brook Falls
4.03.4 mi / 1174 ft gainHiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...Read more -
Voluntown, Connecticut
Hike Pachaug State Forest Trails
5.03.6 mi / 200 ft gainLawden Brook Trail Loop is a 3.6 mile loop hike that takes you by a lake located near Voluntown, Connecticut.Read more -
Salisbury, Connecticut
Explore Riga Falls
The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...Read more -
Kent, Connecticut
Hike the Ridge Loop Trail, Macedonia Brook SP
3.0For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...Read more -
Mount Washington, Massachusetts
Mount Frissell and Brace Mountain Loop Trail
5.08 mi / 807 ft gainMount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.Read more -
Great Barrington, Massachusetts
Hike Monument Mountain
4.02 mi / 720 ft gainAt 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...Read more -
North Stonington, Connecticut
Hike Narragansett Trail
4.010.7 mi / 1 ft gainNarragansett Trail is a 10.7 mile point-to-point hike that takes you by a lake located near North Stonington, Connecticut.Read more -
Mount Washington, Massachusetts
Guilder Pond and Mount Washington Lookout Trail
3.92 mi / 909 ft gainGuilder Pond and Mount Washington Lookout Trail is a loop trail that takes you by the lake located near Copake Falls, New York.Read more -
Stockbridge, Massachusetts
Laura's Tower and Ice Glen
5.02.4 mi / 676 ft gainYou will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods. You will reach a split in the trail, a left will take you...Read more -
Douglas, Massachusetts
Hike the Coffeehouse Loop, Douglas State Forest
3.02.2 mi / 500 ft gainDouglas State Forest is located off of Rte 16 in south central Massachusetts. To access trails and the lake, head to the parking area on Wallum Lake Park Road. From the parking lot, you can access the Coffeehouse Loop Trail, as well as a few other shorter trails by the lake. The Coffeehouse Loop ...Read more -
North Stonington, Connecticut
Hike Wyassup Lake
5.02.4 mi / 278 ft gainWyassup Lake is a 2.4 mile out and back hike that takes you past great forest setting located near North Stonington, Connecticut.Read more -
Groton, Connecticut
Hike Sheep Farm
3.01 mi / 91 ft gainSheep Farm is a 1 mile loop hike that takes you by a waterfall located near Groton, Connecticut.Read more