Pittsfield, Massachusetts
Looking for the best photography in Pittsfield? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Pittsfield. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Photography Spots in and near Pittsfield
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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 -
Tannersville, New York
North Mountain
4.76.16 mi / 1060 ft gainHave you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills. Par...Read more -
Palenville, New York
Kaaterskill Falls via Laurel House
4.51.67 mi / 360.89 ft gainThis short hike is one of the most popular in the Catskills — and for good reason. From the Laurel House Road Trailhead, it’s less than a mile round trip to reach Kaaterskill Falls, New York’s tallest two-tiered waterfall, with a dramatic 260-foot drop into a rocky amphitheater. The trail itse...Read more -
Haines Falls, New York
Fawns Leap
3.5Please be respectful if visiting this local swimming hole. Pack out what you pack in, carry out others' trash, and familiarize yourself with Leave No Trace principles. Hidden in the Catskill Mountains is one of the coolest cliff jumping locations I have ever been to. The first time I went was a...Read more -
Altamont, New York
Wolf Creek Falls Preserve White Trail Loop
3.01.93 mi / 256 ft gainOver 3 miles of trails provide access to all parts of the preserve, and end up winding through mixed terrain including a wetland, waterfalls, and old stone walls. The property crosses the Bozenkill Road at two points on either side of private parcels (with beautiful homes), so be vigilant there; ...Read more -
Kent, Connecticut
Explore Kent Falls
5.00.75 mi / 250 ft gainEvery now and then you need a day to rest those sore muscle from all your recent adventures. The only issue is, you don't want to sit around inside, you want to be outside. Insert a trip to Kent Fall State Park. The perfect rest adventure day.Located 1 hour and 45 minutes north of New York City i...Read more -
Elka Park, New York
Hike to Huckleberry Point
4.54.5 mi / 644 ft gainThis is a 4.5 mile hike that is great for hikers of all skill levels. Because it is short and not overly difficult, beginners will enjoy this hike. There are some steep sections that will get your heart pumping, though, and a stunning payoff is waiting for you at the end.From the trailhead, follo...Read more -
Elka Park, New York
Hike Twin Mountain
6 mi / 1586 ft gainThe DEC Parking lot, is located at the very end of a dead end, along Prediger Rd. Start at the trail head to the right of the trail kiosk and sign in sheet. The trail starts out very easy going as you approach the base of Twin. At mile 0.25, you’ll hit a junction where you’ll turn RIGHT towards T...Read more -
Elka Park, New York
Devil's Path to Devil's Tombstone
5.011.9 mi / 4475 ft gainThe Eastern half of Devil's Path has four major summits: Indian Head, Twin, Sugarloaf and Plateau. Each summit is a straight climb up and down, then back up to as much as 3,900 ft. There are some sparse sections of level ground, but most is a steep descent uphill or steep slide downhill. Your ...Read more -
Elka Park, New York
Devil's Path in the Catskills
4.022.04 mi / 7733 ft gainDevil's Path is roughly more than 24 miles long, althought it feels like an eternity of milage. Going thru the summits of Indian head, Twin, Sugarloaf, Plateau, Hunter, and Westkill Mountains. Its brutal. Its painful, Its unique. Be prepared for anything and everything. You will encounter wild l...Read more -
Simsbury, Connecticut
Hike to the Heublein Tower on Talcott Mountain
4.32.54 mi / 404 ft gainThe Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...Read more -
Windham, New York
Escarpment Trail
21.97 mi / 5282 ft gainThe Escarpment Trail runs the length of the Catskill Escarpment. The Escarpment rises steeply from the valley below forming the northeast corner of the Catskill Mountains. It offers great views toward the Adirondack Mountains to the north and the great Hudson River to the east. The trail is moder...Read more