Windham, Connecticut

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 clear...

For this 1-mile hike, you can park at the Purgatory Chasm Visitor Center. From there hit the trail and explore the unusual gap between the tall granite walls, which might be adorned with climbers. Great for all ages and dogs are welcome too. The trail is open March-November.

Park at the lot at the corner of Staples Lane and County Street. From here you can access the Blackstone Gorge Trail. Dogs are allowed on leash, and you can enjoy various paths along the river or through the forest. At multiple points you can find yourself looking down at the Blackstone River fro...

Enders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut.  Enders has a good sized parking lot directly on Route 219.  From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...

Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...

Sleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...

Since I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...

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...

Whiting Street Reservoir Loop is a loop trail that takes you by a lake located near Holyoke, Massachusetts.

In order to reach the Lighthouse you must walk along the trail that begins at the end of Corn Neck Rd. This walk is along the beach and then veers off to the left once you get closer to the light house (the seventh picture shows the start of the walk). It's only a half mile to the light house, bu...

Just 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...

The Montauk Point Lighthouse is one of the main attractions of "The End" of Long Island, but I've only ever walked around it on the cliff walk.When you get to the lighthouse, you can park in the parking lot (depending on when you go there may be a $8 fee). Right along the edge overlooking the wa...

The 3.5 mile Cliff Walk is a National Recreation Trail in a National Historic District. I chose to start at the western end of Easton's or First Beach at Memorial Blvd. and walk south. The first two-thirds of the walk is very easy walking conditions. Parts of the southern half of the walk are...

I've never actually been into the Shadmoor State Park, but you can climb up and onto the bluffs from the beach easily; well kind of easily.Most of the parking lots along the beach require Hamptons residency tags, so you can't park right next to beach entrances... bummer. We typically park along ...

Block Island, a small island off the coast of the Rhode Island mainland, is well-known as a local summer playland. Tourists typically go to the quaint New England island in the summer months for the biking, hiking, sailing, kayaking, fishing and 17 miles of beaches.Although you can bring a car o...

A trip to Aquidneck Island would not be complete without a quick walk around Sachuest Point. I highly recommend this hike at sunrise, but any time of the day (or year) is great! This nature preserve is home to a large population of tourist-friendly deer, and is visited every winter by at least tw...