Top 5 Favorite Hiking Trails

Nov 8th 2023

Top 5 Favorite Hiking Trails

Short trails, long trails and everything in between–these are our favorite hikes.

The team here at TrailHeads are outdoors enthusiasts, and we’re so lucky that there are so many great places to walk, hike, trail run and more where we’re based, in Connecticut. Did you know that CT was ranked the #1 state for hiking in 2023? This guide spotlights our top five favorite hiking trails in Connecticut, but we’ve included some of our other favorite hikes in the U.S. and abroad at the end.

1. Best Long Hike: Appalachian Trail

We can’t talk about long hikes in Connecticut without mentioning the Appalachian Trail. Clocking in at roughly 2,190 miles, the Appalachian Trail (AT) is one of the United States’ long trails and is part of what’s known as the Triple Crown of hiking (the other two trails are the Continental Divide National Scenic Trail and the Pacific Crest Trail). The AT travels through 14 states, including Connecticut!

People hiking the entire distance in a single attempt are called “thru-hikers.” Most hike the AT northbound (or “NOBO”), starting in Georgia in the spring and finishing in Maine in the fall. Check out our complete guide for hiking the Appalachian Trail for beginners.

Section hiking the AT

Not everyone who hikes the AT is a thru-hiker. For most people, dropping everything to hit the trail for six months is out of reach. That’s why section hiking the AT–hiking sections over time to cover the entire distance–is a goal for many. Logistics and planning is just as robust (if not more!) than those who thru-hike it because of the extra travel required to get to start and end points. Section hiking the AT can take years, but it’s a worthy goal for those with the drive to make it happen!

Some people who live in states the AT travels through might just hike the miles within their state. For example, CT is home to more than 50 miles of the AT.

Appalachian Trail: Connecticut Section

  • Distance: 53.1 miles roundtrip
  • Difficulty: hard
  • Trail type: point to point
  • Elevation gain: 11,204 feet
  • Dogs: allowed on leash

Day hiking the AT

There are plenty of folks who just hit up short portions of the AT without the goal to finish it end-to-end. Because it intersects with so many local trails across 14 states, hopping on for a quick day hike is a great way to experience the AT. We especially love the section near our office in Kent, CT, that goes up to St. John’s Ledges and Glacier Rock via the AT.

St John’s Ledges and Glacier Rock via the AT:

  • Distance: 8.6 miles roundtrip
  • Difficulty: hard
  • Trail type: out and back
  • Elevation gain: 2,680 feet
  • Dogs: allowed on leash

2. Best Medium-length Hike: Windsor Locks Canal Trail

We love out-and-back trails because you have so much flexibility to pick the distance you’d like to hike. That’s why we love the Windsor Locks Canal Trail in Suffield, CT, near the northern border of the state, just over the border from Springfield, MA. This paved trail travels along the Connecticut River for 4.3 miles, one way–double that for 8.6 miles total. You can turn around at any point, making this hike as short or long as you want. With views of the canal and river, it’s a popular spot for birding, biking and walking and is open from April 1 through November 15.

Windsor Lock Canal Trail:

  • Distance: 8.6 miles roundtrip
  • Difficulty: easy
  • Trail type: out and back
  • Elevation gain: 114 feet
  • Dogs: allowed on leash

3. Best Short Hike: Sleeping Giant Tower Trail

Located near Hamden, CT, Sleeping Giant State Park is home to the popular Sleeping Giant Tower Trail. This easy out-and-back is kid- and dog-friendly, so bring the whole family for a lovely afternoon in nature. According to, Sleeping Giant received its name thanks to local Native American creation stories. This land is Quinnipiac, Paugusset and Wappinger. Stories say this giant rock formation embodied Hobbomock, an evil spirit who became angry at the neglect of his people.

Atop Sleeping Giant sits a tower that was built in the late 1930s by the Civilian Conservation Corps. You can walk up into the tower, and views of Long Island Sound can be seen from the top. Vehicles with CT plates get into Sleeping Giant State Park for free, but out-of-state visitors must purchase a day pass.

Sleeping Giant Tower Trail:

  • Distance: 3.1 miles roundtrip
  • Difficulty: easy
  • Trail type: out and back
  • Elevation gain: 597 feet
  • Dogs: allowed on leash

4. Best Waterfall Hike: Kent Falls Loop Trail

The Kent Falls Red and Yellow Loop Trail is a short but sweet hike with observation decks that offer spectacular views of upper and lower Kent Falls–Connecticut’s tallest waterfall, standing at an impressive 240 feet as water cascades towards the Housatonic River. In addition to the falls, the trail is a great spot for bird watching, hiking with your dog and exploring with the whole family.

Vehicles with CT plates get into Kent State Park, located in Kent, CT, for free, but out-of-state visitors must purchase a day pass. Bring a picnic lunch and hang out for a bit. This hike clocks in at just under a mile, but is rated moderate because of the elevation gained in such a short distance. You can extend your hike using other trails inside of Kent Falls State Park. Or, head to St. John’s Ledges just 20 minutes down the road for extra miles.

Kent Falls Red and Yellow Loop Trail:

  • Distance: 0.8 miles roundtrip
  • Difficulty: moderate
  • Trail type: loop
  • Elevation gain: 255 feet
  • Dogs: allowed on leash

5. Best Views: Jones Mountain Preserve Vista Trail

For lovely views of an idyllic New England town nestled in a valley, check out the Jones Mountain Preserve Vista Trail in New Hartford, CT. This loop trail follows an old carriage road marked with red blazes and signage, and offers views of New Hartford, rolling hills and Farming River. We recommend hiking this trail in fall during peak leaf-peeping season for views of foliage across the valley. Jones Mountain is popular for hiking, snowshoeing and cross-country skiing.

Bring your dog, but stay on the trail, wear hunter orange and familiarize yourself with hunting season. Sections of the trail border private hunting property.

Jones Mountain Preserve Vista Trail:

  • Distance: 2.6 miles roundtrip
  • Difficulty: easy
  • Trail type: loop
  • Elevation gain: 387 feet
  • Dogs: allowed on leash

Bonus Trail Picks

There are tons of amazing hikes to do all over the United States and the world, so here are a few that we’ve done or are on our bucket list.

United States

  • The Presidential Traverse: Located in the White Mountains of New Hampshire, this hike is approximately 23 miles over the summits of peaks named after U.S. presidents, including Mount Washington which stands at an impressive 6,288 feet, the highest mountain in the northern East Coast. Part of the “Presi Traverse” is along the AT. This hike can be done in 1-2 days and is rated hard for its elevation gain and very rocky terrain through the northern part of the Granite State. Dogs are welcome, but the terrain can be tough on paws.
  • Vernal and Nevada Falls via Mist Trail: This popular trail in California’s Yosemite National Park is a challenging, 6.4-mile loop that has a little bit of everything: forest, lakes, river, wildflowers, wildlife and, of course, waterfalls. The best time to visit is in spring and early summer when snowmelt from the mountains runs off and makes the falls full. This trail includes rocky terrain, stairs and switchbacks. Because it’s located inside a national park, this loop trail is not open to dogs.
  • Bright Angel Trail: Visitors to Grand Canyon National Park’s South Rim love heading to the Bright Angel Trail. This 15.3-mile out-and-back is unique for its views, shade and access to potable water. It’s great for new hikers and families heading into the Canyon for the first time because you can customize the distance by turning around at any point and there are rest houses along the way. However, it’s still a challenging trail, and it’s important to go prepared. It could also be turned into a thru-hike when connected to other trails. Check out these hiking guides before you go.
  • Calico Tanks Trail: If you’re in Las Vegas, NV, and need a break from the hustle, bustle and lights, head west to Red Rocks Canyon National Conservation Area. Calico Tanks Trail is a moderate 2.3-mile out-and-back with sweeping vistas of rock formations in a very popular area for hiking and running. The best times to visit this trail are October through May. Dogs are welcome, but must be on a leash.
  • Emerald Lake Trail: This popular, scenic trail is located in the heart of Rocky Mountain National Park, near Estes Park, CO. Hikers are treated to three pristine mountain lakes, starting with Nymph Lake, then Dream Lake and finishing at Emerald Lake. This 3.2-mile, out-and-back trail is moderate with some steep sections. Visitors from sea level should plan to hike slower than normal, take breaks and drink plenty of water when hiking at high elevations. Extra mileage can be added hiking over to Lake Haiyaha or looping around Bear Lake by the trailhead. Dogs aren’t allowed in the national park.
  • Angels Landing Trail: Zion National Park is home to this trail, located near Springdale, UT. It is a technical, challenging route with steep drop-offs, very narrow sections and scrambling packed into a 4.3-mile out-and-back trail. However, hikers are treated to river views, wildflowers, wildlife spotting and incredible views of Zion Canyon. This hike requires a permit, and because it’s inside a national park, pups aren’t allowed on the trail.


  • Inca Trail to Machu Picchu: The Inca Trail is a multi-day, 20-mile trek in the Peruvian mountains connecting Machu Picchu from the Sacred Valley of the Incas. Hikers get to experience a subtropical jungle full of flora and fauna, and archaeological sites. This trek requires an accredited agency for guiding services. It’s a popular bucket-list hike for people around the world.
  • Camino de Santiago Frances: Also known as the French Way, the Camino Frances follows a 550-mile Christian pilgrimage route starting in France and finishing at the Cathedral of Santiago de Compostela, in the center of Galicia, Spain. Every spring and summer, many people make the pilgrimage for spiritual growth alongside hikers and cyclists following the same route. The French Way is on the World Heritage List by UNESCO.
  • West Highland Way: In the highlands of Scotland is a 96-mile long trail that is popular with hikers, trail runners, equestrians and cyclists. The West Highland Way starts just outside of Glasgow in Milngavie and travels north to Fort William, terminating at the base of Ben Nevis, the highest mountain in the British Isles. Thru-hikers have the choice to camp or book stays in hostels and inns along the way. The best months to hike this trail are June and September.

Check out our blog for more tips to help you take the trail less traveled.