Sheffield, Massachusetts
Top Spots in and near Sheffield
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Sheffield, Massachusetts
Race Brook Falls
4.02.47 mi / 1145 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 -
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 -
Salisbury, Connecticut
Bear Mountain Loop
4.76.05 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 -
Mount Washington, Massachusetts
Bash Bish Falls
4.30.75 mi / 295 ft gainBash Bish Falls is a spectacular 60-foot waterfall located on the Massachusetts-New York border in the southern Berkshires. This popular destination offers easy hiking access and stunning natural beauty, making it perfect for families and casual hikers. Parking Options Massachusetts Side: 0...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
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 -
Copake, New York
Bash Bish Falls from Taconic State Park
1.53 mi / 167 ft gainBash Bish Falls from Taconic State Park is an out-and-back trail that takes you by a waterfall located near Copake, New York. Swimming is not permitted at Bash Bish Falls.Read more -
Norfolk, Connecticut
Campbell Falls
4.00.99 mi / 161 ft gainCampbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....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 -
Great Barrington, Massachusetts
Hike Monument Mountain
4.52 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 -
Canaan, Connecticut
Explore Great Falls
3.00.5 miStumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.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 -
Sandisfield, Massachusetts
Buck River Swimming Hole
4.00.3 mi / 250 ft gainThis swimming hole is 7-feet deep. At the top of the swimming hole is a 12-foot waterfall with slide down. Parking: The swimming hole is located between Sandisfield Town Office and the post office. There is one dirt pull-off space near the swimming hole. The easiest parking is at the Town Offic...Read more -
Hudson, New York
High Falls Conservation Area Loop
1.41 mi / 194 ft gainHigh Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.Read more -
Sharon, Connecticut
Hike the Pine Knob Loop, Housatonic Meadows SP
5.02.5 mi / 770 ft gainThe Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick woods filled with vistas, wild flowers and tons of wild life. You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...Read more -
Stanfordville, New York
Explore Wethersfield Estate & Gardens
The Wethersfield Estate is a beautiful estate and property located less than 2 hours north of New York City. The gardens are expansive and extremely beautiful, open to the public each day from noon to 5pm (COVID-19 hours). Additionally, there are trails for horseback rides, carriage rides, dog-wa...Read more