7 Cute Small Town Drives In Massachusetts
Massachusetts is a New England dream, offering scenery, history, food, and adventure along its scenic roads. If you have an itch for a road trip but are not in the mood for a long, arduous journey, there are ample opportunities to take in the charm of the state without investing more than a few hours. From the Mohawk Trail to the Essex Coastal Scenic Byway and Berkshire Mountain routes to riverside and island drives, Massachusetts roads take you to darling towns waiting to be explored. Read on for seven cute small-town drives in Massachusetts perfect for your next jaunt.
Mohawk Trail
Running just under 70 miles, the scenic Mohawk Byway was once used as a footpath by Native Americans. The road was designed to attract tourists to the area back in 1914. Route 2 is a bit of a thrill ride, taking you through the Connecticut River Valley to the Berkshire Mountains with switchbacks and a stunning hairpin turn with distracting views. Three summits offer exceptional lookouts, including the highest point at Whitcomb Summit, offering long-range views of the Green Mountains and the Hoosac Range.
Along the Mohawk Trail, the Bridge of Flowers in Shelburne Falls is one of the sweetest sights in Massachusetts. The historic site was created by the Shelburne Falls Women’s Club in 1928, who transformed an abandoned, weedy trolley bridge into a living work of art, planting hundreds of flowers. The newly renovated bridge now features flowering trees, shrubs, perennials, vines, bulbs, and annuals overlooking the Deerfield River.
Get even better views of the Deerfield River in Charlemont as the river flows along the Byway. The town is also home to a 900-pound bronze casting, Hail to the Sunrise by sculptor Joseph Pollia, honoring the Five Indian Nations of the Mohawk Trail. The Mohawk stands with his arms uplifted, overlooking the river to the east.
The Berkshire Mountains Route 7
The Berkshire Mountains are known for quaint small towns and captivating scenery. A road trip along U.S. Route 7 has massive appeal to nature and art lovers, who can take a pleasant 40-mile drive from Great Barrington to North Adams in a little over an hour. Vogue magazine thinks Great Barrington might be the most charming town in the Berkshires. The town also happens to have one of the best roadside food shacks, which lives up to the town’s bougie sophistication. Burgers from the adorable little Bistro Box provide the perfect fuel for your Berkshires road trip.
Once you've had your lunchtime fix, head north to Lenox, a Gilded Age gem with a rich arts and cultural scene. Visit the Frelinghuysen Morris House & Studios to tour the Art Deco summer home of two New York artists and view their spectacular collection of Modernist art.
Pittsfield’s lovely historic buildings include The Lichtenstein Center for the Arts, where you can explore the exhibitions, nine artist studios, a ceramics studio, and galleries. Although one might expect to find the iconic work of artist Roy Lichtenstein here, the center is not associated with the pop artist and instead is named after town art benefactor Kitty Lichtenstein.
Finish your journey near the Vermont border in North Adams, a lovely town on the Hoosic River. Discover well-known and emerging artists at MASS MoCA and be blown away by immersive, large-scale installations perfectly suited to the 300,000 square foot raw industrial space.
North Shore Route 127
Traveling from Beverly to Rockport along the North Shore is a coastal adventure offering plenty of scenery and fun stops along the way. Route 127’s scenery around Cape Ann makes this drive special. Covering 40 miles, the drive is about an hour. However, you have to factor in the time to visit attractions and scenic overlooks to make the most of the short drive.
Before you head out from Beverly, pop into the cozy Beantrust for coffee and baked goods to go and take in the views from Lynch Park. Carry on to Manchester-by-the-Sea, to Coolidge Reservation, where the views from the lawn offer spectacular ocean views.
Perched on the coastline in Gloucester sits the enchanting Hammond Castle, a must-see attraction according to the Travelers’ Choice Awards. The historic landmark built in the late 1920s offers tours of the medieval-style castle, lovely ocean views, and various collections and exhibits.
Your journey ends in Rockport, where you can stroll the town’s Bearskin Neck and treat yourself to fresh local seafood at My Place by the Sea, one of Zagat’s ten best destinations for oceanfront dining on the Massachusetts coast.
Essex Coastal Scenic Byway
This 90-mile scenic byway takes you to 14 coastal communities along Route 133. The period architecture, scenery, and sites between Lynn and Salisbury offer something for everyone to enjoy.
Kick off your journey at the Lynn Stories Mural at Lynn’s Central Square to explore the town’s history in a colorful painted tapestry. If you have never visited Salem, its witchy history and beautiful historic buildings are a must. The Witch House tends to win out as one of the few sites directly related to the Witch Trials, combining everyday life in the period home with the owner, Judge Jonathan Corwin, who conducted the trials.
Essex is all about the antiques and is often thought of as America’s Antique Capital. There are over 30 shops within a mile of each other where you can browse for hours searching for art, furnishings, and collectibles. Head to the finish line in Salisbury for a well-earned oceanside meal. While many hotspots shut down after the summer rush, you can rely on Seaglass Restaurant & Lounge to offer a warm welcome all year round. Their panoramic ocean views, fresh seafood, and drinks made them an OpenTable Diner’s Choice Winner in 2024.
Blackstone River Valley
Following the Blackstone River from northern Rhode Island to south-central Massachusetts, this picturesque route tells the story of America’s industrial history. History buffs will revel in this short and sweet historic corridor along Route 146 from Millville to Millbury, covering about 20 miles.
Start in Millville, which is home to one of the best-preserved locks from the Blackstone Canal. Next, you'll head to Uxbridge. Hike along the historic canal once used for trade in the 1800s at the Blackstone River and Canal Heritage State Park. River Bend Farm is an example of historic Blackstone Valley farms where fields, open pastures, stone walls, and preserved historical sites tell the stories of the valley and town’s farming during the birth of the Industrial Revolution.
Take 122 from Uxbridge to Whitinsville to explore a quintessential mill village. Whitinsville's Downtown Crossroads Historic District encompasses the town’s six intersections, where you can discover historic properties directly tied to the mill village’s growth, including Whitinsville Brick Mills & Forge, Cotton Mill, and Memorial Town Hall. Then take Main Street to get back on 146 and head to Millbury. The walking tour in this town completes your adventures exploring the Blackstone River Valley’s history, including the S&D Spinning Mill.
Martha’s Vineyard Tour
Any drive on this charming island will take you to quaint little towns with scenic views. However, traveling about 20 miles from Oak Bluffs southeast to Edgartown and then west to Chilmark is the perfect way to spend the day on Martha's Vineyard. Oak Bluffs sits at the northeastern side of the island, where you can discover the sweet little Gingerbread Cottages at The Campground. These 1800s beauties are maintained by the Martha's Vineyard Camp Meeting Association. Take the walking tour to admire the ornate architecture, fanciful colors, and whimsical gardens.
Follow the coastal route to Edgartown to stroll the red brick sidewalks, admiring the window displays offering everything from fashion to jewelry and gourmet food and wine to home décor and art. Pop into Behind the Bookstore Café for a coffee and fresh baked goods to enjoy on your short drive to West Tisbury. If you are looking for iconic white steepled churches, roadside farm stands, and homes with weather-worn cedar shingles, West Tisbury has it all. Explore the tranquil gardens at Polly Hill Arboretum, where serene meadows, stunning displays of azaleas, camellias, and rhododendrons, and varied trees and blooms change the landscape throughout the seasons.
Your final destination at Chilmark offers a combination of stunning ocean and rolling countryside, where you can discover an authentic working fishing village, Menemsha. Feast on fresh lobster and seafood, watch the fishing boats come in with their catch, stroll along the pier, laze on the beach, and chat with seascape artists.
Jacob’s Ladder Scenic Byway
This easy drive from Lee to Russell takes you through the Berkshires along Route 20. Covering about 30 miles, the changing landscape, views of the Westfield River, and quaint small towns are perfect for fall drives. Lee is the logical jumping-off point, as it is often thought of as the Gateway to the Berkshires. This riverfront town sits on the Housatonic with a lovely main street made for leisurely strolls. The Starving Artist Café & Creperie is your first stop for an exceptional crepe breakfast, followed by coffee for the road.
Follow Route 20 to reach Becket State Forest. Stretch your legs hiking the enchanting woodlands and forests where the diverse landscape offers stunning vistas and picturesque scenery, including rippling brooks, wildlife, and ponds. Then carry on to Chester to find sustenance after your tiring hike. Carm’s is conveniently located right on 20, where you can find old-school diner-style burgers and shakes and a selection of creative sandwiches in a former Mobil gas station still sporting its iconic red-winged horse.
Next stop, Huntington. Take a detour along Route 112 Scenic Byway to explore Huntington’s farms and scenic views, and hit the trails at Littleville Lake’s 1,567-acre park. Wander the old cart roads along the lake and take in the picturesque vistas. Get back on Route 20 for the last legs of the drive to Russell, where the experience is all about the forest and Westfield River views.
These seven cute small-town drives in Massachusetts are filled with classic New England white-steepled churches, quaint eateries, historic sites, and natural beauty. From island views on Martha's Vineyard to Industrial Revolution history in the central part of the state to forest drives in Western Massachusetts, there's an itinerary for every driver. You can follow these routes at your own pace, whether you want to make a day of it with stops along your journey or are simply in the mood for a leisurely drive.
