Milford, Connecticut
Looking for the best hiking in Milford? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Milford. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Milford
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Washington, Connecticut
Hike Meeker Trail
3.3 mi / 639 ft gainMeeker Trail is a 3.3 mile out and back hike that takes you by a lake located near New Preston, Connecticut.Read more -
Middlesex County, Connecticut
Hike to Glen Falls
5.00.75 miAccessing Glen Falls may be a little tricky at first. Parking will be very minimal, you will park on Grist Mill Ln. Hop onto the road and you will see the trail map on the left side. The adventure begins when you cross the street and go through the gate with the yellow blaze symbol. Keep followin...Read more -
Patchogue, New York
Fire Island's Watch Hill
4.02 miIf departing from NYC, catch the early LIRR train from Penn Station (or Atlantic Terminal) towards Patchogue. You may have to transfer at both Jamaica & Babylon, but it's an easy hop across the platform. Trip will take approximately an hour and a half and cost around $15, Off Peak, each way. ...Read more -
Carmel Hamlet, New York
Ninham Mountain Fire Tower
5.01.23 mi / 367 ft gainThis is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...Read more -
Rye, New York
Hike the Marshlands Conservancy Loop
4.01.55 mi / 125 ft gainLocated along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...Read more -
Glastonbury, Connecticut
Hike the Cotton Hollow Nature Preserve
5.03 miThere are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...Read more -
Shelter Island, New York
Hike through the Mashomack Nature Preserve
10 miJust a short ferry ride from the Hamptons, South Ferry Road is exactly where it sounds; very close to the South Ferry of Shelter Island. The parking lot of Mashomack Preserve is marked by a large sign. When you walk in, you'll see a large nature center. Sign in at a clipboard at the table out fro...Read more -
Kent, New York
King's Chamber and Moose Hill Loop
3.14 mi / 499 ft gainKing's Chamber and Moose Hill Loop is a loop trail that takes you by a lake located near Carmel, New York.Read more -
East Haddam, Connecticut
Chapman Falls
4.00.55 mi / 49 ft gainIf you map to Chapman Falls in East Haddam, CT, you will be brought to a parking lot opposite from the waterfall in Devil's Hopyard, a beautiful Connecticut state park. Once there, it's only a few minute walk down a very clear trail to the base of the 60 foot falls. There's plenty of room to se...Read more -
Pleasantville, New York
Swan Lake Loop
5.01.37 mi / 85 ft gainSwan Lake Loop is a loop trail that takes you by a lake located near Hawthorne, New York.Read more -
Briarcliff Manor, New York
Hike Kate Kennard Trail
1.8 mi / 140 ft gainIf you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...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 -
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 -
Hopewell Junction, New York
Lake Canopus Viewpoint
4.02.07 mi / 148 ft gainIts a great place to explore as it has a beautiful calm lake especially in the fall, the reflection of the water and the awesome colors are unbelievable. Its a short hike but you certainly could go further up. Parking is free by the road, hike towards the lake about a mile or so. The sound of bi...Read more -
Hopewell Junction, New York
Beaver Pond via Appalachian Trail
5.03 mi / 400 ft gainBeaver Pond is a small body of water created by a dam that was constructed during the days of iron ore mining in the area. The pond is crystal clear and has a wonderful tree line right on the water. The best time to visit here is early morning in the fall. With the leaves changing color they m...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