Massachusetts' Underrated Berkshire Mountain Town Has A Laid-Back Downtown And Scenic Trails

The Berkshires lure people away from the city with their pretty mountains, cute towns, and endless outdoor activities. However, one of those towns, Dalton, is constantly overlooked. But with its historic downtown and picturesque hiking trails, it shouldn't be — it's time to give this low-key destination another try.

This little spot in Western Massachusetts is considered a transition spot between the manufacturing hub of Pittsfield and the quiet woods of the Berkshire Mountains. Dalton was founded as a farming and small factory community in 1784, and it grew after Crane & Co. (a paper mill that made stationery and currency paper for the U.S. Treasury) was established along the East Branch of the Housatonic River in the early 19th century. Many of the buildings from this time period are now part of the Cranesville Historic District, which is part of the National Register of Historic Places, while the small town of Dalton is now home to fewer than 6,200 people.

The closest airport to Dalton is across the New York border in Albany. Its Albany International Airport (ALB), which receives nonstop flights from mostly East Coast cities, is less than 45 miles away. You can also ride Amtrak from Boston to Pittsfield. The Lake Shore Limited train departs from the city's South and Back Bay Stations. From Pittsfield, a buzzing artsy city with world-class food and fun, it's then only a 5-mile drive to Dalton.

As you start exploring Dalton, it's impossible to miss the historic buildings throughout town. There are gravesites from as early as 1801 in the Main Street Cemetery, which has a Gothic chapel beside it. Unlike the cemetery chapel, the nearby First Congregational Church is still in use. Its current building is from 1812, though a church was originally built here in 1785. You also shouldn't miss the Fitch-Hoose House, from 1846, since it was a stop on the Underground Railroad.

Though some of the old buildings in Dalton look much the way they did centuries ago, others have changed with the times. Before building their paper mill, the Crane family established a large farm. Holiday Brook Farm now offers a cafe, farm tours, and a farm stand that sells farm-grown meat and vegetables. Then Sugar Hill, an estate completed in 1909, was the home of Winthrop Murray Crane, who grew the family's paper mill before becoming the Governor of Massachusetts. The Georgian Revival mansion has been transformed into an assisted living community.

Mixed in with all of this history, you'll find casual dining spots. The Dalton Restaurant is a classic diner that serves comfort food. Its hearty breakfasts will fuel you for the day ahead. Then, Shire Tavern brings people together with pub food, games, and live music. It's the perfect spot to recount your adventures. Don't be surprised when conversations veer towards hiking, since the Appalachian Trail runs right through the center of Dalton.

Though the Appalachian Trail, one of the longest hiking trails in the world, is known for its scenic mountain views, the 2,198-mile trail also passes through 56 towns en route from Georgia to Maine, and Dalton is one of those towns. The trail runs through the Day Mountain Wildlife Management Area, a popular birding spot, on the southeast edge of town before following High Street into Dalton. The historic buildings and restaurants on Main Street are just a short detour from the trail.

The popular Appalachian Trail isn't the only scenic trail in Dalton. Wahconah Falls State Park might be a small state park at only 48 acres, but it leads to a stunning waterfall. The trail to Wahconah Falls is an easy, 1.1-mile, out-and-back path. You'll hike through a hardwood forest and along a stream to reach the 40-foot waterfall and the Windsor Reservoir Dam.

There's also The Boulders, which extend into neighboring Lanesborough and Pittsfield. This is a 645-acre rocky area with almost 7 miles of trails — its longest one, the Blue Trail, climbs to a lookout point with impressive views of the Taconic Mountains to the west. In the same direction, you'll find another type of adventure. Bousquet Mountain, Massachusetts' oldest ski area, is less than 10 miles away. Or, if you're looking for a way to relax, Lenox, a quiet romantic retreat nestled in New England's rolling hills, is just a bit farther. This part of the Berkshires might not remain underrated for long.