The Most Scenic Drives in Massachusetts

The most populous state in New England is packed full of diverse scenery making Massachusetts road trips among the most pretty in the country. A mixture of a gorgeous coastline, rolling forests and beautiful national parks means there is a drive for all occasions.

Many of the drives make for ideal leisurely day trips with plenty of stops included along the way. The lighthouse road trip is also ideal to build a longer multi day vacation around to see the best the state has to offer.

The thing about Massachusetts road trips is that there is always a jaw dropping view around the next corner. Pack up the car and get ready to enjoy.

The Best Massachusetts Road Trips

Cape Ann

This picturesque coastal route will bring you from the town of Salem to Rockport on the tip of Cape Ann – the perfect day trip! You’ll drive through through Gloucester, a historic fishing town; Essex, with cute antiques stores, and finally Rockport, a scenic fishing village with winding streets, seafood shacks and quaint stores.

Distance: 21 miles

Route highlights: Gloucester, Halibut Point State Park, Rockport

When to do it: Year-round

Northern Berkshires

One great way to take in the stunning Berkshire scenery is on a scenic drive. This route through the Northern and Central Berkshires takes you by the beautiful mountain panorama surrounding Pontoosuc Lake, public beaches, through the area’s farmlands and forests and plenty of stop-offs in local towns along the way.

Distance: 53 miles

Route highlights: Savoy Mountain State Forest, Historic Deerfield, North Adams

When to do it: Year-round, although fall foliage is breathtaking.

Old King’s Highway

Travellers cruising along this highway can see hundreds of historic sites, from sea captain houses, to pilgrim churches, to other historic buildings. Other scenic viewing points include cranberry bogs, salt marshes, and preserved farmlands. The route winds its way through some of the oldest villages in America, including Bourne, Sandwich, Barnstable, Yarmouth, Dennis, Brewster and Orleans.

Distance: 59 miles

Route highlights: Town Neck Beach, Sandy Neck Beach, Nickerson State Park, Wellfleet Bay Wildlife Sanctuary

When to do it: Summer, Spring, Fall

Central Hills Loop

Want a fall foliage road trip? Hop in the car and take in the beautiful autumn landscape in Central Mass on this beautiful drive. The scenic byway of Route 122 is a 40 mile rural route running north and south from Paxton to Orange. The route connects forests and rivers for plenty of hiking, wildlife watching, boating, and biking opportunities.

Distance: 57 miles

Route highlights: Quabbin Reservoir, Gilbertville (covered bridge), Hamilton Orchards

When to do it: Fall

Southwest Berkshires

This is a stunning drive at all times of the year, but especially during foliage season when you can take in the riot of colour offered by the Berkshires landscape. Start in Sheffield, the oldest Berkshire County town that has become a mecca of antiques shops, stopping off for waterfall walking trails at Bish Bash Falls before following the Konkapot River Valley to Mill River.

Distance: 27 miles

Route highlights: October Mountain State Forest, Pittsfield State Forest, Lenox, Hancock Shaker Village

When to do it: Spring, Summer, Fall

Lighthouse Road Trip In Massachusetts

No trip to Massachusetts is complete without seeing at least one of the state’s historic lighthouses, so why not see as many as you can and make a road trip out of it? There’s Boston Light, the oldest lighthouse in America, established in 1716. Highland Light on Cape Cod, the first light seen on a voyage from Europe to Boston. Brant Point Light on Nantucket Island has been moved and rebuilt more than any other. Race Point Light, in Provincetown, is open to the public for overnight stays.

Distance: 263 miles

Route highlights: Cape Cod (Highland) Light, Nauset Light, Plymouth (Gurnet) Light, Minot’s Ledge Light, Boston Light, Eastern Point Light

When to do it: Spring, Summer, Fall

Mount Greylock

At 3,941 feet, the summit of Mount Greylock stands as the highest point in Massachusetts! This route, which is accessible by vehicle from May through October, starts in Lanesborough and carves a path through the state reservation, offering breathtaking views all along the way to North Adams, the iconic Berkshires town that marks its end.

Distance: 17 miles

Route highlights: War Memorial Tower, The summit

When to do it: May-October