Massachusetts' 'Most Famous School Town' Blends Historic Sites, Schools, Hiking, And Equestrian Trails

Nestled approximately 40 miles northwest of Boston is a charming New England village where historic schools, downtown character, and abundant green space converge. Officially incorporated in 1655, Groton's rivers, lakes, wildlife, and farmland facilitated its development into the largest town in all of Middlesex County by area. At the heart of Groton sits The Groton Inn, one of America's oldest inns. With a rich history dating to 1678, the property hosted the likes of Paul Revere and other key Revolutionary-era figures, making visitors feel as though they've been transported to another era. If comfortable rooms, a complimentary breakfast, and a cozy restaurant serving up delicious fare sound appealing, don't miss out on the opportunity to stay at this timeless property. 

Along Main Street, visitors can marvel at Federal, Greek Revival, and Victorian architecture — a testament to Groton's unmistakable character — plus a slew of shops and restaurants to keep everyone in the family occupied. Enjoy delicious entrees such as garlic-and-herb chicken and bone-in rib-eye (which pair nicely with picturesque views) at Gibbet Hill Grill, a standout farm-to-table restaurant with its own multi-acre livestock and produce farm. Those who are up for breakfast any time of day will feel at home at Blackbird Café, open daily until 2:30 p.m. Then, stop by Coco Home Décor & Gifts, where shoppers can snag one-of-a-kind items at great prices. 

For more browsing, consider making time for Paris-inspired Back Bay, one of Boston's most coveted neighborhoods with upscale shopping. The closest major airport to Groton is Logan International Airport in Boston, about a 45- to 75-minute drive depending on traffic. For regional or private flights, Worcester Regional Airport serves as a secondary option, 37 miles southwest.

Groton, often dubbed "Massachusetts' Most Famous School Town," is home to two historic boarding schools that draw scores of visitors annually. Established in the wake of the Revolution, Groton Academy was incorporated in 1793 with Governor John Hancock's signing of its first charter and was later renamed Lawrence Academy in recognition of its founding benefactors. The Groton School, founded in 1884 by Endicott Peabody, has fostered a global reputation for rigorous college-preparatory education, counting eminent individuals like Franklin Delano Roosevelt among its alumni. Amble through the grounds and see why Architectural Digest included it in its list of the most beautiful private high schools in the country.

But there's far more to the town's history than its academic heritage. The First Parish Church of Groton, built between 1754 and 1755 and restyled in 1839 with a Greek Revival portico, stands as a distinctive example of Georgian and Greek Revival architecture, notable for its clock tower and steeple. The Bennett-Shattuck House, built around 1812 and listed on the National Register of Historic Places, is representative of rural Federal-period architecture. The Boutwell House, constructed in 1851 and once home to politician and abolitionist George S. Boutwell, fuses Greek Revival and Italianate styles. It currently serves as the headquarters for the Groton Historical Society, whose extensive collections shine a light on Groton's past. Just outside the center, the stone remains of Bancroft's Castle on Gibbet Hill recall the grand ambitions of its builder, General William Bancroft.

After sightseeing, stop for a drink at Bell in Hand, one of America's oldest continuously operating taverns with a rich Boston history. The establishment was founded in 1795 by the city's first town crier, Jimmy Wilson. With so many fascinating Revolutionary-era sites to explore along Boston's Freedom Trail, the hourlong drive is well worth it! 

Whether you're into hiking, skiing, horseback riding, farming, nature-watching, or all of the above, Groton offers seamless connections to the outdoors. With over half its land under conservation, the town has over 100 miles of trails that weave through wetlands, farms, forests, and river valleys, forming one of the most extensive networks in Massachusetts. Groton's landscape is made distinctive by its rolling drumlin hills, a rare geological formation left behind by glaciers. In fact, Autumn Hills Orchard, which grows more than 30 varieties of apples, sits atop three of these hills and offers sweeping views of the surrounding mountains.

At Shepley Hills Conservation Area, long-established bridle paths wind alongside hiking loops, culminating in a historic soapstone quarry that's worth a stop. These trails allow walkers and horseback riders to share the land in a rural, bucolic setting just minutes away from Groton's center. Moreover, the Nashua River Rail Trail offers a scenic route for walking, biking, or horseback riding along its 12.5 lush miles.

Lawrence Woods, one of Groton's conservation parcels, provides flat trails beneath white pine canopies on 26 acres along the Nashua River floodplain. Open from dawn to dusk, it's popular for dog walking, skiing, hiking, and riding. Meanwhile, the Groton Town Forest— with more than 16 miles of trails and drumlin hills — hosts guided hikes. The Groton Town Forest Trail Races, which require an entry fee and award prizes to first-place finishers, are perennial crowd pleasers. While there, be on the lookout for red foxes, beavers, deer, and other wildlife. If time allows, make the hourlong drive to Maudslay State Park, Massachusetts' unique state park with beautiful 19th-century gardens and trails.