New England · Berkshires to Cape Cod · Statehood 1788
Massachusetts
State
Field Guide
The place where much of American history starts, on a coastline of dunes and lighthouses, with the Berkshire hills out west. You can walk the Revolution in the morning and be on a Cape Cod beach by dinner.
Updated October 2026 · Written by artist Nick Scacco
Classic Experiences
01.
Downtown Boston · Charlestown
Walk the Freedom Trail
A red-brick line on the sidewalk links 16 sites from Boston Common to Charlestown, among them the Old State House, Paul Revere's house, Old North Church, and the USS Constitution, the oldest commissioned warship still afloat. It is a two-and-a-half-mile walk that is easy to do in a day or split across two. Start at Boston Common early, and take a break for a cannoli in the North End.
02.
Outer Cape · Eastham to Provincetown
Explore Cape Cod National Seashore
The Outer Cape's Atlantic side is a long, protected stretch of dunes, marsh and ocean beach, established as a national seashore in 1961. Climb the dunes at Province Lands, walk the Great Island trail, or watch the surf at Coast Guard Beach near Nauset Light. Water at the ocean beaches is cold and the surf can be rough, so check conditions and lifeguard hours before swimming. Provincetown, at the tip, is a lively end to the drive.
03.
The Berkshires · Adams
Drive to Mount Greylock
Mount Greylock is the highest point in Massachusetts, topped with a granite war memorial tower with long views across five states on a clear day. A seasonal summit road makes it an easy drive, and the Appalachian Trail passes over the top for hikers. Drive down into North Adams to see MASS MoCA, one of the largest contemporary art museums in the country. The Berkshires are at their best in late September and early October.
Little-Known Gem
Dogtown Common and the Babson Boulders
Cape Ann · Gloucester and Rockport
Inside Gloucester's wooded interior is a roadless stretch of boulder-strewn forest where a colonial settlement was gradually abandoned and left to the trees. Cellar holes still mark where houses once stood. In the 1930s, a local businessman paid stonecutters to carve motivational words into boulders along the trails, so you can hike past giant rocks inscribed with single-word messages. Few of the tourists on Cape Ann have found it.
Massachusetts Travel Questions
What are the best places to visit in Massachusetts?
Three classics are the Freedom Trail in Boston, Cape Cod National Seashore, and Mount Greylock in the Berkshires. Dogtown Common on Cape Ann is the quieter gem.
How long is the Freedom Trail?
It is about 2.5 miles and connects 16 historic sites from Boston Common to Charlestown. You can walk it in a day or split it across two.
When is the best time to visit Cape Cod National Seashore?
June through September has the warmest weather for the ocean beaches. The water is cold and the surf can be rough, so check conditions first.