Natchaug / Nipmuck Trails

The 32-mile hike on the Natchaug / Nipmuck Trails in Connecticut meanders through woods still bearing stone walls and cellar holes from colonial days. The hike can be completed in 2-4 days.

Region: New England (Connecticut State Forests)
Length: ~32 miles (2-4 days)

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Physical Difficulty: Easy

Little elevation gain.
Meandering path through long-abandoned Connecticut farms, with stone walls and cellar holes still visible.
Passes through one of the largest contiguous forests in Southern New England.

Logistical Difficulty: Easy

Permits required for overnight camping; no dispersed camping allowed.
Point-to-point hike. Use a two-car shuttle, or leave a car at one trailhead and Uber to the other.
Well-marked, easy-to-follow route.
Plentiful water.

Season: Year-round

Elevation (Average): 800 feet
Total Elevation Gain: 4,000 feet

Hiking the Natchaug / Nipmuck Trails

You won’t find soaring vistas or epic climbs on the Natchaug and Nipmuck Trails.

What you will find are dazzling thickets of flowering mountain laurel in the spring, trees ablaze with color in the fall, and remnants of farms long ago abandoned to the hardscrabble New England soil.

My favorite trail in Connecticut’s 850-mile blue-blazed trail system is the Natchaug Trail in eastern Connecticut that traverses an area called the Last Green Valley, a National Heritage Corridor. Hooking up with the Nipmuck Trail creates a two- to four-day hike for all levels of backpackers.

I recommend starting at the southern terminus at James L. Goodwin State Forest, leaving what I consider to be the best sections for last.

From the Goodwin parking lot the trail quickly meets Pine Acres Pond—a popular bird-watching spot—and briefly follows the shoreline before connecting with the Airline State Park Trail, an old railroad bed now used for hiking and biking. Signs along the trail describe the trees bordering the trail.

The trail diverges from the Airline and weaves through woods filled with stone walls and an occasional old cellar hole. You’ll soon pass nearly 100 acres that was heavily logged after trees were devastated by gypsy moths in the late 2010s.

The trail continues past Black Spruce Pond, another bird-watching area.

After passing from Goodwin into Natchaug State Forest you’ll soon climb Orchard Hill, at 675 feet the second-highest hill on the trail. There’s an overlook with a bench and a modest view.

The hike through Natchaug really gives a feel for life when farms dominated these woods, including an old mill site along a brook.

Before reaching the first overnight camping spot you’ll pass through Nathaniel Lyon Memorial State Park, birthplace of Nathaniel Lyon, the first Union general killed in the Civil War. The chimney from the house still stands.

A few hundred feet past the chimney is the General Lyon Shelter, with water available from a small stream just before the shelter.

Day two takes you through more hardwood forests laced with stone walls and cellar holes, with a brief walk along the Still River. Cross the river on a bridge on Pilfershire Road, then bear left onto General Lyon Road. (Lyon’s grave is in a cemetery across the road. And if you’ve binge-snacked through your sweet treats or want a cold drink that isn’t water, the Corner Market—the only store near the trail—is about a quarter mile to the right on Lyon Road / Route 189.)

The trail (bearing left) follows General Lyon Road / Route 189 for about half a mile before re-entering the woods. From there the trail meanders easily through the woods before crossing Route 44 and descending to Bigelow Brook. You’ll cross a short section of the The Hole in the Wall Gang Camp, a summer retreat for seriously ill children that was founded by the late Paul Newman.

The trail continues along Bigelow Brook, where a bench next to the brook provides a quiet place to relax and enjoy the burbling water. It’s an easy place to sit and lose track of time.

The Natchaug Trail ends several miles later at its junction with the Nipmuck Trail. An approved tentsite is about three-quarters of a mile south on the Nipmuck Trail, and is a good place to stop if you’re making this a three-day hike. The water supply is a stream about 100 feet before the tentsite.

If you’re making this a two-day hike, continue north on the Nipmuck Trail.

The two trails in this area coincide with sections of the Old Connecticut Path, first used by Native Americans and then settlers traveling from Boston to Hartford in one of the first major inland migrations by Europeans.

If you stopped for the night at the tentsite, backtrack to the Nipmuck / Natchaug Trails junction. Heading north, the Nipmuck Trail soon enters Yale-Myers Forest, 7,840 acres managed by the Yale School of Forestry and Environmental Studies. Near the northern end of the forest is an area called Tree Heaven, with benches for classroom work and tree lots marked for management and ecological studies.

The trail also passes Walker Mountain, about a quarter mile west on a marked side trail. The barely noticeable summit is 1,087 high feet—the highest peak along the trails—with limited views and remnants of an old fire tower.

After descending the ridge that the trail follows through the northernmost section of Yale-Myers Forest you’ll cross Route 171 into Nipmuck State Forest. Breakneck Pond and the northern campsites are a few miles farther north.

If you’re heading to your car on day three, take the white-blazed Connector Road from the southern end of the pond to the hiker parking lot on Bigelow Pond. If you’re staying the night for a four-day hike, the Connector Road passes the Breakneck South Shelter while the Nipmuck Trail continues north to the Breakneck East Shelter. The South Shelter is tucked away from the trail, while the East Shelter is right on the trail, but has a great view of the pond. The tentsite is on the Breakneck View Trail on the western shore of the pond. View the trails map here.

How to Get to the Natchaug / Nipmuck Trails

Closest Cities: Hartford, Connecticut; Worcester, Massachusetts; Providence, Rhode Island.

All three have small regional airports: Bradley International Airport, Windsor Locks, Connecticut; T.F. Green Airport, Warwick, Rhode Island; Worcester Regional Airport, Worcester. No public transportation to any of the trailheads.

Driving There: The trail starts just off Route 6 in the south and Route 171 in the north, crosses state Routes 44 and 189, and smaller roads. Dirt pull-offs at trail road crossings.

Where to Park

Southern Terminus: James L. Goodwin State Forest on Route 6 in Hampton, Connecticut. Large parking area. Let the people in the visitors center know that you’re parking overnight for a multiday hike. The Natchaug Trail starts at the parking area.

Northern Terminus: Bigelow Hollow State Park on Route 171 in Union, Connecticut, just a few miles from Interstate 84. Entrance fee to the park for nonresidents, no fee for Connecticut residents. Leave a note on your dashboard that you’re hiking on a multiday trip. Trails lead from the large hiker parking lot at the northern end of Bigelow Pond to Breakneck Pond and the northern terminus of the Nipmuck Trail at the Massachusetts / Connecticut border. The trails around Breakneck Pond can be confusing so it’s a good idea to download a map.

When to Hike the Natchaug / Nipmuck Trails

Fall: Bright colors, cool temperatures, and mostly dry weather bring out the best on Connecticut’s hiking trails. This is a good time for a multiday hike on the Natchaug and Nipmuck Trails, especially midweek. Expect weekends to be busy. November and December are deer hunting season, which is allowed along the two trails.

Winter: Trail conditions can range from deep snow to frozen, open paths. After fall, this is my favorite trail time.

Spring: Wet, buggy, wide range of temperatures. The trails may be muddy, but there are no tough stream crossings.

Summer: Hot and humid, which wouldn’t be so bad if there were deep river pools to cool off in. There aren’t.

Two-Day NOBO Itinerary

Day One: Goodwin State Forest to General Lyon Shelter, ~7.5 miles.

Day Two: General Lyon Shelter to Bigelow Hollow State Park hiker parking lot, ~24 miles.

Three-Day NOBO Itinerary

Day One: Goodwin State Forest to General Lyon Shelter, ~7.5 miles.

Day Two: General Lyon Shelter to Nipmuck Trail tentsite, ~12 miles

Day Three: Nipmuck Trail tentsite to Bigelow Hollow State Park hiker parking lot, ~13 miles

Four-Day NOBO Itinerary

This adds a loop around Breakneck Pond and back to your car on the fourth day.

Day One: Goodwin State Forest to General Lyon shelter, ~7.5 miles.

Day Two: General Lyon Shelter to Nipmuck Trail tentsite, ~12 miles

Day Three: Nipmuck Trail tentsite to Bigelow Hollow State Park East Shelter, ~13 miles

Day Four: East Shelter to Massachusetts border on Nipmuck Trail, Breakneck Pond View Trail along the western shore of the pond, Connector Road to parking lot, ~5 miles.

Natchaug / Nipmuck Trails Terrain

The trails are mostly dirt-carpeted forest paths and old woods roads through undulating terrain. Boulders the size of small cars dot the landscape. You’ll cross several streams, some with bridges, but none with difficult water crossings.

Logistics: Permits, Camping, Water

Permits: The Connecticut Department of Energy and Environmental Protection issues permits for the General Lyon Shelter on the Natchaug Trail in Natchaug State Forest, the South and East shelters and a primitive tentsite on Breakneck Pond in Nipmuck State Forest, and a primitive tentsite on the Nipmuck Trail three-quarters of a mile south of the junction of the Nipmuck / Natchaug Trails. Natchaug State Forest also has horse-packing sites. Fee for nonresidents to enter Bigelow Hollow State Park.

Camping: Overnight camping is allowed only at the three shelters and two campsites. Water and fire pits, no privies.

Water: Plentiful. The trail briefly follows streams and passes several ponds.

Know Before You Go

Weather: Typical New England fare. Cool and dry in the fall; cold, although snow is increasingly scarce, in the winter; wet and buggy in the spring; hot and humid in the summer.

Route Finding: The trail is easy to follow, with blue blazes marking the way. Volunteers maintain the trail, and section maintenance varies depending on the volunteers. The Connecticut Walk Book, available through the Connecticut Forest and Parks Association, is the definitive guide for the state’s blue-blazed trails.

Beware: Ticks are plentiful along the trail—Lyme disease was first identified in Connecticut—and permethrin-treated clothing and insect repellent are good protection. Poison ivy crowds the trail at some road crossings.

Animals: Bears, bobcats, moose and deer roam these forests. Protect your food from bears. Moose and bobcat sightings are rare. Deer are everywhere.

History: The Natchaug Trail passes through General Nathaniel Lyon Memorial Park (birthplace of the first Union general to be killed in the Civil War) in Eastford. Northern sections of the Natchaug and Nipmuck Trails briefly follow the Old Connecticut Path, first used by Native Americans and then traveled in the 1630s by European settlers from Boston who founded Hartford.

The Last Green Valley: 1,100 square miles covering 35 towns in south-central Massachusetts and northeastern Connecticut that are 77% forests and farms. Known as the last stretch of dark night sky in the coastal sprawl between Boston and Washington, D.C. But be aware that the trails are never far from the distant hum of cars and trucks, especially in the northern section near Interstate 84.

Cell Phones: Reception is good on the trails, but spotty in Bigelow Hollow State Park. The Bigelow hiker parking lot is a black hole for cell reception.