Massachusetts Travel Guide

Massachusetts is small enough that you can land in the morning and be somewhere entirely different by lunch. Boston to Provincetown is about 115 miles of road, Boston to the Berkshires about 135, and Salem is 16 miles up the coast. So distance is not what makes or breaks a trip here. Dates do: ferry reservations that open in January, a single month when Salem becomes unrecognizable, and about two weeks in October when the whole state changes color.

Boston sits a third of the way up the coast and works as the hinge for everything else. East of it, the arm of Cape Cod curls out into the Atlantic with Martha’s Vineyard and Nantucket offshore. North, the old shipping towns of the North Shore run up to the New Hampshire line, Salem among them. West, past Worcester and the Connecticut River valley, the land climbs into the Berkshires, which feel closer to Vermont than to the coast. Four trips, one small state, and a rental car needed for three of them.

Boston: how long, and what for

Give Boston three days. It’s the most walkable big city in the country, the Freedom Trail links 16 historic sites over two and a half miles of red line in the sidewalk, and Boston Common at the start of it has been public land since 1634, which makes it the oldest public park in the United States. Fenway Park, the North End’s Italian food, the Museum of Fine Arts and the university campuses across the river in Cambridge fill the rest.

Getting into town cheaply comes down to two things. The Silver Line SL1 bus from Logan Airport is free from every terminal and runs to South Station downtown, so the first ride of your trip costs nothing. And once you’re in town, the subway (everyone calls it the T) is $2.40 a ride, local buses $1.70, with a 7-day pass at $22.50 if you’ll be riding twice a day or more. You don’t want a car in Boston. Pick it up the morning you leave.

Cape Cod and the islands: the part you book first

The Cape is a hook of dunes, kettle ponds and beach towns, and its outer arm is protected as the Cape Cod National Seashore: forty miles of sand facing the open Atlantic. Six of the Seashore’s beaches charge $25 a day per vehicle in season, running from late May to mid-September, with a $60 annual pass that pays for itself on day three; bring a card, because the park takes no cash. Provincetown at the tip is the liveliest town on the Cape and the easiest to reach without driving, since fast ferries run there from Boston in the summer.

The islands are where planning gets real. Martha’s Vineyard and Nantucket are reached by boat, and the Steamship Authority is the operator that carries vehicles. Its summer reservations open in the depth of winter and disappear fast: for the 2026 season, car slots to Nantucket went on sale at 8 a.m. on 27 January for travel between 14 May and 22 October. If you are reading this in June and hoping to take a car across in August, that ship has sailed, and the honest advice is to leave the car on the mainland anyway.

Go over as a foot passenger instead. Hy-Line’s high-speed boat covers Hyannis to Nantucket in about an hour, from $52 one way or $97 round trip for adults in 2026, and both islands are set up for people who arrive without a vehicle: bikes for rent at the dock, shuttle buses, taxis, and towns you can walk end to end. Nantucket’s cobbled center and Brant Point Light are twenty minutes on foot from the pier. On the Vineyard, the gingerbread cottages of Oak Bluffs are barely further.

Which island? Nantucket is smaller, further out, more expensive and more uniform - gray shingles, cobblestones, whaling money. The Vineyard is six times the size with six distinct towns, from the fishing village of Menemsha to the clay cliffs at Aquinnah, and it takes a day or two longer to see properly. Day trips work for either, but you’ll spend three hours of that day on boats.

Salem in October, and Salem the rest of the year

Salem in October is a different city. The Haunted Happenings season runs the whole month, downtown streets close, and by the final weekend the place is packed shoulder to shoulder. The city responds with satellite parking lots at Salem State University and elsewhere, plus free shuttles into downtown on weekends. Take the hint. Driving in is the worst option; the commuter rail from Boston’s North Station runs to a station a few minutes’ walk from the museums, and in season the ferry from Long Wharf takes about 55 minutes across the harbor.

It’s worth knowing what actually happened here, because the souvenir shops muddle it. In 1692, nineteen people were hanged and one, Giles Corey, was pressed to death under stones. Nobody was burned at the stake - that was Europe. And the accusations started in Salem Village, a farming settlement that is now the separate town of Danvers, several miles from the downtown that sells the witch hats. The serious places to understand it are the Witch Trials Memorial beside the Old Burying Point, the Peabody Essex Museum, which holds original court documents, and the 1668 House of the Seven Gables.

Come in any other month and Salem is a handsome, uncrowded seaport with a maritime national historic site on the waterfront and hotel rates that haven’t tripled.

The Berkshires: the other Massachusetts

Two hours west of Boston the state turns into hill country, and the culture follows it out there every summer. Tanglewood in Lenox is the summer home of the Boston Symphony Orchestra, and the tradition is to buy a lawn ticket rather than a shed seat, bring a picnic and listen to a world-class orchestra lying on the grass. In North Adams, MASS MoCA occupies a 19th-century mill complex and shows contemporary art at a scale no conventional museum can: $25 for adults, closed Tuesdays.

Around them sit the Clark Art Institute in Williamstown, Edith Wharton’s house at The Mount, Norman Rockwell’s museum in Stockbridge, and Mount Greylock, the highest point in the state at 3,491 feet, with a road to the summit. The Berkshires are also the one region where a summer weekend books out months ahead, because Tanglewood fills every inn between Great Barrington and Williamstown.

When to go

Fall is the season people plan around, and the color moves east across the state rather than north to south. The Berkshires usually peak around the second week of October, most of the rest of Massachusetts in the last week, and the coast and Cape Cod about a week after that, which is why a late-October trip can give you bare hills in Lenox and full color on the Cape in the same week. The state’s Department of Conservation and Recreation runs a foliage tracker that updates through the season; check it before you fix dates, because peak moves by a week or more with the weather.

Summer is beach season, and it is also when the islands cost the most and the Cape’s single highway backs up on Friday afternoons. Cross the bridges early or late, never at 4pm on a Friday in July. Winter closes a lot of the Cape and most island restaurants, but Boston keeps working and the Berkshires switch to skiing. Spring is quiet and cheap, with cold water and a decent chance of rain - fine for museums and towns, poor for beaches.

Car or no car

You need a car for the Berkshires, the North Shore beyond Salem and most of the Cape, and you do not want one in Boston or on the islands. The efficient sequence is city first with no vehicle, then pick up a rental car at the airport or a downtown desk on the way out. Salem is the one exception in reach of the city without wheels, thanks to the commuter rail and the seasonal ferry.

Distances are short but the roads are not fast. Route 6 down the Cape is a single artery with traffic lights, and summer weekends turn the last 30 miles into an hour and a half. The Mass Pike west to the Berkshires is the opposite: dull, quick, and worth taking rather than the pretty back roads if you’re driving it after dark. If you’re combining Massachusetts with New York, the Berkshires sit two hours from the Hudson Valley, which makes an easy loop with New York State.

Book two things before anything else: the island ferry if you’re going in summer, and a Salem hotel if you’re coming in October. Everything else here can be decided a week out.

Read also

• The city in detail: things to do in Boston
• Next state over: New York State travel guide
• The other end of the Northeast corridor: things to do in Washington DC
• Browse more US states and US cities