Hidden Between Three New England Rivers Is A Walkable Massachusetts City With A Picturesque Downtown

When traveling along the East Coast, it's easy to fill a road trip with visits to charming seaside New England towns and breathtaking national and state parks. Whether you're planning a peaceful escape in nature or a "Gilmore Girls"-inspired getaway, Greenfield, Massachusetts is a historic and picturesque city you won't want to miss.

Located in Franklin County at the confluence of Deerfield River, Connecticut River, and Green River, Greenfield is roughly a two-hour drive from Boston, Massachusetts and a one-hour drive from Hartford, Connecticut. Greenfield is also well connected by train, with an Amtrak station located at the John W. Olver Transit Center. If you're staying overnight, there's a well-reviewed Hampton Inn & Suites, the charming Brandt House bed and breakfast, and many vacation rentals on Airbnb.

Visitors to Greenfield often appreciate its history. The city was first settled in by the English in 1686, and some of its historic buildings date back to the late 1700s and early 1800s. It also boasts a charming small-town feel and picturesque downtown area. Consider timing your visit during the Franklin County Fair in September or the Bee Fest in May, which celebrates the city's historic ties to the beekeeping industry.

An ideal afternoon in Greenfield will likely include strolling around the Crossroads Cultural District, a walkable neighborhood with historic buildings, charming boutiques, and fantastic local restaurants. History buffs can visit the Museum of Our Industrial Heritage or take a self-guided walking tour of 12 landmarks that were on the Underground Railroad or are otherwise important to abolitionist history, each commemorated with a mural.

Shoppers will want to check out the Vintage Valley Trail, a local nickname for popular antique, vintage, and secondhand stores in Franklin County. Whitney Hill Antiques is frequently recommended, as are Sweet Phoenix, Federal Street Books, and Greenfield Records. Foodies can enjoy a meal at the popular farm-to-table restaurant Hope & Olive, sample clam strips or lobster rolls at Pete's Seafood, or try locally brewed beer at The People's Pint or Four Phantoms Brewery.

Greenfield also has a thriving arts and culture scene. You can catch a movie at the independent Garden Field Cinemas, see a play performed by the Silverthorne Theater Company, or enjoy an outdoor concert at Energy Park. If you're visiting on a Saturday in April through October, don't miss the weekly Greenfield Farmers' Market, which often features live entertainment as well as local produce and handcrafted goods. 

Nature enthusiasts should consider hiking in Greenfield's picturesque Rocky Mountain Park and Poet's Seat Tower, an observation point that offers stunning views of the surrounding countryside. It's one of the most popular spots in the area for both locals and visitors. Outdoorsy travelers might also want to go hiking or birdwatching at Highland Pond. According to a TripAdvisor review, Highland Pond is an "impressive trail for forest hiking" with "a great deal of local flora and fauna." In the summer, you can visit the Green River Swimming and Recreation Area, which features an area for swimming, a sandy beach with a play area for toddlers, athletic courts, and plenty of picnic spots.

If you can't get enough of New England's charming towns and cities, Greenfield is located a little over an hour's drive from two other hidden gems. Stay in Massachusetts a little longer and pay a visit to quaint Sturbridge, a "portrait of old New England charm," or Williamstown, known for its vibrant arts scene.