How to Spend One Week in Massachusetts

Boston, Massachusetts

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New England is a beautiful place to visit, and thanks to its four distinct seasons, you can experience it in different ways based on when you plan your trip and the areas you explore. Spending one week in Massachusetts and getting a taste for this New England state’s highlights is doable with a little road tripping here and there (and maybe a couple ferry rides). 

Despite being located on the far eastern side of the state along the water, you’ll find that Boston is a good home base for your week in Massachusetts. Most of what you’ll want to see is within driving—or ferry—distance from the city, and this is also where you should plan to fly in and out of via Logan International Airport.

Note that while below will offer the best options for exploring the entire state in a week, if you’re visiting in the summer, you may want to spend more time doing coastal activities. If that’s the case, sub out one of the road trips (for example, the Berkshires) for more time on Cape Cod, Martha’s Vineyard, or Nantucket. Or simply take a day to relax at one of Massachusetts’ best beaches

Similarly, if you’re visiting during fall’s peak foliage season, that may warrant spending more time in Western Massachusetts, as it’s one of the best places to see foliage in New England. This part of the state is also where you’ll find more outdoor activities like hiking and skiing.

Here’s one sample itinerary for how to see Massachusetts in a week, but of course, you can always make it your own using this as a starting point. This guide maps out your trip in a way that both limits and includes renting a car, as most of the itinerary can be accessed either way.

01 of 07

Day 1: Boston

Boston's Faneuil Hall

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Plan on flying in and out of Boston’s Logan International Airport, as that’s where you’ll find the most flight options at the best prices. Book a hotel in the city, keeping in mind you want to be somewhat close to the attractions you’re looking to see, but also that Boston is quite walkable and easy to get around with public transportation and Uber.

For your first day in the city, start with Boston’s iconic Freedom Trail, which is a 2.5-mile brick path leading you to many historical sites either on your own self-guided tour or with a guided tour. The Freedom Trail is not a loop, as it starts at the Boston Common, the oldest park in the country, and ends in Charlestown, home of the Bunker Hill Monument and the USS Constitution. However, you can follow the Freedom Trail in either direction or pick and choose which pieces are most of interest to you if time is limited.

Taking the Freedom Trail will allow you to hit several popular tourist attractions and historical landmarks, from the Faneuil Hall Marketplace and the Old North Church to the Paul Revere House, State House, and the site of the Boston Massacre.

02 of 07

Day 2: Boston

Boston Tea Party Ships & Museum

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Take the second day in the city to visit one or two of Boston’s top museums. Families will want to check out the Boston Children’s Museum, throw replica tea bags overboard at the Boston Tea Party Ships and Museum, or experience STEM-focused, interactive exhibits at the Museum of Science. For those more into art, head to the Museum of Fine Arts, Isabella Stewart Gardner Museum, or the Institute of Contemporary Art.

Pop over to Newbury and Boylston Streets, along with the Prudential Center and Copley Place, for some shopping in the Back Bay. There are plenty of restaurants in this area as well that make for good lunch or dinner spots. Another option is to go to one of Boston’s breweries and try out local beers alongside a meal. More and more are popping up in neighborhoods like Fort Point, a newer area next to the Seaport

Lastly, if it’s a beautiful day and you only want to see one museum (or none at all), book a ticket on the famous Duck Tour to see Boston in a boat on wheels.

03 of 07

Day 3: Provincetown or Other Cape Cod Towns

Provincetown, Cape Cod, Massachusetts

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One of the best day trips from Boston is visiting Provincetown at the tip of Cape Cod, a town known to locals as “P-Town” via the 90-minute ferry departing from Boston through the Bay State Cruise Company. Because of this, you won’t have to rent a car yet—and you can avoid Cape traffic. (It would take you 2.5 hours to get there driving from the city without accounting for traffic, which you’re bound to hit during warm weather months.) If you choose the car-free route, we recommend you omit Martha’s Vineyard (or Provincetown if you really want to get to the islands) and spend more time in one of the other listed destinations.

Provincetown is known as an LGBTQ-friendly resort community, with beaches and a downtown area filled with restaurants, art galleries, and boutiques. As a bonus, the town is known to be dog-friendly, so go ahead and bring your four-legged friend. Also, consider stopping by the nearby Truro Vineyards of Cape Cod to sample local wine paired with cheeses and other snacks (or bring your own lunch to enjoy on the picnic tables). If it’s beach weather, visit the Cape Cod National Seashore.

04 of 07

Day 4: Martha's Vineyard

Martha's Vineyard beaches

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Martha’s Vineyard and Nantucket, islands off the coast of Massachusetts, are two popular destinations for Bostonians and tourists alike during the summer months thanks to their picturesque beaches. For a short trip, Martha’s Vineyard will be your best option, as it’s a shorter ferry ride than Nantucket. Before booking, keep in mind that if you’re visiting Massachusetts during the winter months, you’ll likely want to forgo the Martha’s Vineyard trip, as the islands are quiet at this time of year.

The ferry departing from Woods Hole in Falmouth—the “fast ferry” at 45 minutes—will take you to Vineyard Haven in Martha’s Vineyard, where you’ll find shops, restaurants and more. Visitors also enjoy checking out the towns of Oak Bluffs, home to the island’s Gingerbread Cottages, and Edgartown, both of which offer their own charm. There are beautiful beaches all around the island, including South Beach and also the picture-perfect Aquinnah and Cliffs of Gay Head.

There is no direct ferry from Provincetown to Martha’s Vineyard, which is why you’ll want to have a car to see both. It’s up to you if you bring the car to Martha’s Vineyard or not. The ferry departing from Woods Hole via the Steamship Authority does permit cars, but it can be expensive, and reservations are often needed. You don’t need a car on Martha’s Vineyard if you bring (or rent) a bike or plan to get around by the island’s Vineyard Transit Authority.

If you opt for skipping Provincetown, you can get from Boston to the Martha’s Vineyard “slow ferry” without a car during summer weekends on the CapeFLYER train. This goes from Boston’s South Station to Hyannis, where the Hy-Line ferry departs from, taking about an hour to Oak Bluffs. You can technically do this with the P-Town visit, but you’d have to take the P-Town ferry back to Boston then get on a train to the Martha’s Vineyard ferry, which is a bit of a time suck.

Continue to 5 of 7 below.
05 of 07

Day 5: The Berkshires

The Berkshires in Massachusetts

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Western Massachusetts, particularly to the area known as the Berkshires, is another area you won’t want to miss on your tour of the state. The Berkshires are exceptionally beautiful during peak foliage season. You’ll want to have your camera ready as you drive through the towns, from Stockbridge (one of our picks for the best small towns in the state) and Lenox to North Adams and Great Barrington.

Aside from leaf-peeping, the Berkshires are where you’ll find a wide variety of outdoor activities—hiking, snowshoeing, skiing, cycling, and more—along with music festivals, art galleries, and museums.

If you’re looking for a luxury spa experience, book a night at the Canyon Ranch Lenox. Other recommendations for accommodations include Tourists Welcome in North Adams, the Cranwell Resort in Lenox, Berkshire East Mountain Resort in Charlemont or charming bed and breakfasts throughout the area.

06 of 07

Day 6: Salem

Salem Witch Trials Memorial

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Salem is a coastal Massachusetts town filled with historical landmarks, located 30 minutes north of Boston. Known for the Salem Witch Trials of 1692, this New England town is especially popular during Halloween season, bringing in over 250,000 people each year for the Salem Haunted Happenings, which take place throughout October. If you’re traveling to Massachusetts from late-November to the New Year, they also have a Holiday Happenings festival. 

Salem is a town you’ll want to check out regardless of the time of year, as there is plenty to do from visiting the Salem Witch Museum, Peabody Essex Museum or The House of Seven Gables, to touring the Salem Heritage Trail, which features 127 historical sites across three loops.

07 of 07

Day 7: Newburyport and Depart from Boston

Newburyport, Massachusetts

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A bit further north of Boston is Newburyport, another coastal town and a popular day trip from the city. It’s maintained its historic charm from when it was settled back in 1635 but has been modernized over time. Walk around the town, pop into shops, and grab a bite to eat on the marina. If you have a car, nearby beaches, including Plum Island, are a short drive away.

Newburyport is a 40-minute drive or 32-minute train ride (take the Newburyport/Rockland Commuter Rail line) from Salem. When you’re ready to head to the airport, it will take you under an hour, but be sure to look out for traffic, especially on Fridays and weekends. If you don’t have a car, you can take the C&J non-stop bus service to the airport.

If you prefer to skip Newburyport and get back to the city before your flight, use this time to take a Duck Tour in the morning, walk along Boston’s HarborWalk or explore a neighborhood you haven’t yet seen.

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