Hiking the New England Trail – Best Sections and Tips

Hiking the New England Trail offers an incredible mix of natural beauty and serenity. This trail stretches over 230 miles through picturesque landscapes in Connecticut and Massachusetts, showcasing stunning views of rolling hills, dense forests, and clear streams.

Whenever I’ve set out to tackle a stretch of the trail, I’ve found that each segment of the trail had its own personality. Whether you’re an experienced hiker or just looking for a peaceful escape, the New England Trail has something for everyone. The well-marked paths and diverse terrains make it accessible and enjoyable.

Trail Sections and Routes

The New England Trail is unique in that it is a true Sea-to-Mountain (not white-capped mountains, but still part of the Appalachian range) style thru hike, but it also has lots of smaller hike-able sections along the way that are worth a day hike.  The trail has a variety of terrain and experiences across its sections in Connecticut and Massachusetts. Each section provides unique hiking opportunities, with notable summits and camping options.


east peak
East Peak, CT

Connecticut’s portion of the trail spans approximately 140 miles. It winds through classic New England landscapes, including ridge lines, forests, and river valleys. This section is known for its challenging climbs, particularly along the Metacomet Ridge. Highlights include the breathtaking views from Hubbard Park and the rugged terrain at Ragged Mountain.

The direct path, from South to North, takes you from Guilford to Enfield. In Guilford, you start at the Atlantic Ocean, but soon you will be wandering inland with no sea air around. If you chose the indirect path, you will notice there is a spur from around Rockland up through Middletown. This can be a worthwhile spur, through Miller’s Pond State Park and over Mount Pisgah (not the larger Mount Pisgah in the Great Smoky Mountain area though.)

Not far from the trail’s start around Meridien, is East Peak. It is a great lookout and a good destination in its own right.

North, the trail winds heavily in Central CT before skirting around the western side of the Hartford metro and then straightening out as it heads up toward Massachusetts.

Hikers tackling this part should be prepared for steep ascents and rocky paths. It’s a good idea to break the hike into manageable sections, perhaps starting with easier segments like the Mattabesett Trail. This allows for proper acclimatization to the more strenuous hikes.


Massachusetts adds another flavor to the trail with its 92 miles extending into the Pioneer Valley. Here, the trail offers a mix of wooded paths, farmland, and scenic overlooks. The paths tend to be less rugged compared to Connecticut but still provide moderate challenges.

The trail winds near the Springfield metro before getting more rugged in the Mount Tom and Holyoke Range areas. It then heads in to a rural part of Mass and toward the New Hampshire border, where it ends just past Highway 32. Although the trail kind of ends with a whimper, it connects to the Metacomet- Monadnock Trail continues toward the summit of Mount Monadnock in Jaffrey, NH, about 18 more miles off the New England Trail.

Mount Tom
Mount Tom, MA

Notable segments include Mount Tom and its adjacent reservation area, which boasts sweeping views over the valley. The trail’s passage through the historic town of Amherst provides a pleasant mix of culture and nature, making it a great spot for a lunch break or an overnight stay.

Mount Grace, near the Northern terminus of the trail, is the highest point on the entire trail at just under 1,700 feet.

Best Section of the Trail

If I had to choose a favorite area of the New England Trail, it would probably be the area around Springfield, MA. Even thought it is located relatively close to a medium-sized metro area, the trail in this section has some great overlooks and follows the famed Metacomet Ridge the entire way. Specifically, I’d recommend from the CT/MA state line up through the Mount Tom State Park.  – Mt. Tom, and would make sure you find the cliffs overlooking Easthampton and the Goat Peak fire tower.

This section is challenging due to its elevation changes and rugged pathway. However, for those prepared, it’s an unforgettable experience with some of the most breathtaking scenery on the trail.

A close second for me would be East Peak down in Connecticut.

Notable Summits

Among the trail’s notable summits, several stand out. I’ve mentioned Mount Tom in Massachusetts which provides an excellent vantage point over the Connecticut River Valley.

Bald Mountain in Connecticut offers spectacular views and a sense of solitude. Another highlight is West Peak in Meriden, providing stunning views of the surrounding landscape. Each summit offers a unique perspective and challenge, making them rewarding goals for hikers of all levels.

Camping and Lodging Options

For long-distance hikers, the trail offers several camping and lodging options. There are designated camping areas such as a popular campsite on Metacomet Trail and Highland Pond Shelter in Massachusetts.

Several towns along the trail offer bed and breakfasts, motels, and inns. Amherst in Massachusetts and Meriden in Connecticut are good spots to plan your overnight stays. Always check for required permits in advance, especially for more popular camping sites to ensure availability. This is a trail where, if you aren’t completely ready to live in the wild, you can find some creature comforts in many spots along the way.

Choosing the Right Season

The New England Trail can be hiked in all four seasons, assuming it is not a heavy snow winter, and each season has its advantages and disadvantages. In spring, blooming flowers and mild temperatures make for a pleasant experience. Summer boasts long daylight hours but beware of mosquitoes and ticks, including the risk of Lyme disease. Fall brings cooler weather and beautiful foliage, though the trail might be crowded. Winter offers solitude and pristine snow-covered landscapes, but it requires more gear and preparation to handle the cold.

Holyoke area
Holyoke Area


It is really important to keep ticks away while on the trail. This area is a hotbed for Blacklegged ticks, or Deer ticks, the ones that carry Lyme disease. The best approach is to treat your clothing and footwear with permethrin before you go – one treatment works for a long time. Then, it doesn’t hurt to use a little DEET on your skin during those days when you are hiking through heavier brush.

Always check yourself for ticks at the end of each day.

Permits and Regulations

Different segments of the New England Trail may require specific permissions for camping or parking. Always check for any current trail advisories or closures. Adhering to Leave No Trace principles is crucial to maintain the trail’s natural beauty. Carry out all trash and respect wildlife to ensure the trail remains pristine for future hikers.

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