Ashford, Connecticut

Looking for the best hiking in Ashford? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Ashford. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Ashford

  • Meriden, Connecticut

    Higby Mountain Trail

    2.11 mi / 486 ft gain
    The popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice!  The beginning of the hike is mostly flatter land and an incline w...
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  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
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  • Westerly, Rhode Island

    Napatree Point Conservation Area Trail

    4.0
    3.19 mi / 82 ft gain
    Napatree Point Conservation Area Trail is a loop trail that takes you past scenic surroundings located near Westerly, Rhode Island.
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  • Ashland, Massachusetts

    Hike the Ashland Reservoir Trail

    5.0
    3.2 mi / 68 ft gain
    Park in the lot on State Park Road (see map) to access the trail. It's a popular trail that is dog-friendly. Pay attention to the trail as at parts it is not well marked. 
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  • Meriden, Connecticut

    Hike the Metacomet, Blue, and Yellow Loop

    5.0
    4.5 mi / 976 ft gain
    Start from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...
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  • South Kingstown, Rhode Island

    Osprey Point Loop on Trustom Pond

    4.0
    2.06 mi / 115 ft gain
    Careful on the drive in for deer! From the parking lot head right around the Farm Field Loop Trail then continue to your right down Osprey Point Trail (0.8 miles). This is where you will most likely see the deer up close. Continue to your right to the Osprey Point Overlook, which will (on a clea...
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  • Westminster, Massachusetts

    Summit Mt. Wachusett via the West Side Trail

    5.0
    1.2 mi / 750 ft gain
    Set your GPS to Wachusett Mountain ski area. Coming from Rt. 2 turn onto Mile Hill Rd and look for your first right to take Bolton Rd. Take this road all the way until it intersects with West Princeton Rd. Turn left. and  drive down W Princeton Rd  for 1.2 miles and there should be a small parkin...
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  • Marlborough, Massachusetts

    Hemingway Street Trail

    1.73 mi / 197 ft gain
    Hemingway Street Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Marlborough, Massachusetts.
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  • Jamestown, Rhode Island

    Beavertail Lighthouse Loop

    5.0
    2.35 mi / 95 ft gain
    Rhode Island isn't exactly on everyone's map, I've even met strangers in other parts of the U.S. who have no idea where the tiniest state in the country is. It's usually lumped in with Connecticut and Massachusetts, but for us locals from little Rhody, Rhode Island is it's own world of adventure ...
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  • Deerfield, Massachusetts

    South Sugarloaf Trail

    1.48 mi / 404 ft gain
    South Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.
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  • Cheshire, Connecticut

    Hike to Roaring Brook Falls

    5.0
    1.2 mi / 377 ft gain
    Arriving to the falls, parking is residential but don't worry everyone is friendly. Starting off the hike you will walk past a cool pond where you may be able to see some wildlife. Continuing on, you will follow the marked trail where it will take you further into the woods while gaining elevatio...
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