Massachusetts is known for its incredible scenery, and one of the best ways to see it all is on the road. From the mountains to the coast and everywhere in between, these picturesque drives throughout the state invite you to explore and experience the sights, scenery, and towns along the way at your own pace.
Western Massachusetts
Route 57
One of the most underrated drives in the state, this road is known for its ridge-top views and long stretches through forest and farmland. As one of the more rural areas of Massachusetts, Route 57 has very little traffic, making it a perfect escape from the noise and business of a big city. A great drive at any time of year, the section near Granville is especially beautiful in October.
Route 112
Intersecting with the iconic Mohawk Trail and just south of Route 2, you’ll find deep river valleys and vibrant forested hills in between quaint and unique small towns like Ashfield and Worthington. The rugged hills and curves of this route make it a fun road for motorcycle drivers.
East Mountain Road
The route between Great Barrington and Alford is packed full of open meadows and amazing views of the Berkshire mountains. Along the way you’ll find plenty of historic farmhouses and very little development, making it feel like you’ve driven backward in time. Photographers and artists flock to this road – it’s one of the prettiest and most unique areas in Massachusetts.
Central Massachusetts
Petersham–Hardwick Back Roads and the Quabbin Reservoir Loop
The network of roads around Petersham, Hardwick, and the Quabbin Reservoir are peppered with history. Between historic village centers, you’ll find stone walls, observation towers to view the scenery, wildlife, old-growth forests, expansive water views and very little development. These roads are easily accessible from Worcester, but you’ll feel worlds away from the city.
Route 32 Through the Wachusett Region
The roads right around Mount Wachusett are known for their classic New England scenery – rolling farmland, orchards, and (of course) perfect mountain views. On clear days, you can see all the way to Boston.
North of Boston
Atlantic Avenue, Marblehead
Marblehead is one of Massachusetts’ real hidden gems. This short but spectacular coastal drive is one of the best ways to experience it. The road will take you past historic homes and iconic rocky shorelines, with ocean views along almost the entire way.
Route 133
Connecting Newburyport, Rowely, and Ipswich is a series of roads full of historic farms, expansive tidal marshes, and plenty of opportunities to view wildlife. You’ll also find world famous seafood and some of the best antiquing in Massachusetts!
South of Boston
Route 3A
The salt marshes of Hingham and Duxbury are well known for their seafood, but they are also incredible to look at. Through historic town centers, coastal villages, and working harbors, Route 3A is an underrated way to experience the South Shore – and pick up some oysters along the way.
Jerusalem Road
For any fans of coastal architecture, this is the road for you. Cohasset’s Jerusalem Road is famous for its cliffside waterfront estates.
Cape Cod
Ocean View Drive
Wellfleet’s Ocean View Drive offers exactly that – an amazing way to see the ocean, and the beaches, dunes, and forests that border it.
Shore Road
The drive from Truro up to Provincetown is one of the best places to experience a sunset in Massachusetts. The “hook” part of the Cape is famous for large sandy dunes and ocean views. A quieter road, there are many spots to pull over and just admire the scenery.
No matter what you’re looking for in terms of scenery – forests, mountains, coastlines – Massachusetts has it. On the road, you can experience it all.
