One of the original 13 colonies, Massachusetts boasts historical landmarks dating back to the very beginnings of European settlement in the United States. Boston's Freedom Trail is often the first stop for history buffs and weaves past many of the city’s numerous historic spots. The beautiful beaches of Cape Cod, Nantucket and Martha's Vineyard offer relaxing beach vacations. Here are the best places to visit in Massachusetts.
Best Places to Visit in Massachusetts:
1. The Berkshires
Rating: ★★★★★
The Berkshires is probably most well known for its fall foliage displays. I used to visit the area often during my 10 years of living in NYC. You'll be on the slopes of Green Mountain, surrounded by charming small towns and villages where it's easy to relax and unwind. I enjoyed the concerts by the Boston Symphony Orchestra at the Tanglewoood Music Center in Lenox during the summer. You can browse their upcoming events here.
If you enjoy art, there is the Norman Rockwell Museum, the Williamstown Theatre Festival, and MASS MoCA. I did a lot of hiking in the Berkshires. You can also go hiking, rafting, fishing, kayaking, and golfing, as well as skiing, snowshoeing, and snowboarding in the winter. I enjoy writing about the Berkshires and you can see my longer article here or check out my recent post about Ashfield.
Cost:
$$–$$$ – Lodging tends to be on the expensive side. If you plan a day trip, you don't have to spend money on a room, but many hotels and events have an admission fee.Local tips:
Book early for fall foliage weekends.How to Get to the Berkshires:
Drive from Boston or New York; the region is accessible via I-90. Amtrak and regional buses serve towns like Pittsfield and Great Barrington.2. Cape Cod
Cape Cod is a peninsula that extends out from the State of Massachusetts into the Atlantic Ocean and one of the top Massachusetts destinations. It is an area of sandy beaches, romantic sunsets and windswept dunes. Cape Cod is a natural treasure and features seemingly endless outdoor activities. It is one of the best places in the US for whale watching.
Your best chances of spotting a whale are between March and October. Beyond the beaches that attract many visitors, the forests, marshlands, ponds, and cranberry bogs are just waiting to be explored on foot or by way of the many miles of cycling trails. The towns in Cape Cod are full of history and shopping opportunities at the local boutiques as well as in antique and souvenir shops.
Cost:
$$–$$$ – Lodging and dining range from casual and affordable to upscale coastal inns and fine seafood restaurants.Best time to visit:
- March to October – For whale watching and ideal outdoor conditions.
- Summer – For beach days, festivals, and town events.
- Fall – For fewer crowds and stunning foliage along the coastline.
Local tips:
Avoid peak weekend traffic by arriving early. Visit Wellfleet for oysters, Chatham for charm, and Provincetown for culture.How to Get to Cape Cod:
Drive from Boston (about 2 hours), take a ferry from Boston to Provincetown, or fly into Barnstable Municipal Airport. The Cape Cod Rail Trail also offers bike-friendly access through multiple towns.Map & More Info:
Cape Cod, MA3. Martha's Vineyard
Martha's Vineyard is an island located to the south of Cape Cod. It is a popular summer getaway for the very wealthy and many of the homes on the island are vacation rentals and summer homes, although a few people call Martha’s Vineyard home all year round. The island is primarily a destination where people go to relax and enjoy the beaches and surrounding areas, however the towns do offer a few recreational options.
A small number of boutique shops dot the streets. Visitors can tour the connected Chappaquiddick Island and its lighthouse. The Martha’s Vineyard Playhouse offers weekly entertainment as does the popular summer film festival.
Cost:
$$$ – A high-end destination with luxury rentals, boutique shopping, and elevated dining experiences.Best time to visit:
- Late spring to early fall – June through September is ideal for beach weather, events, and ferry access.
- Early fall – For fewer crowds and perfect coastal foliage.
Local tips:
Book ferry reservations in advance—especially in summer. Consider renting a bike or scooter for a fun and eco-friendly way to explore the island’s towns and scenic spots.How to Get to Martha’s Vineyard:
Take a ferry from Woods Hole on Cape Cod. Advance reservations are strongly recommended during summer months.Map & More Info:
Martha’s Vineyard, MA4. Salem
Salem played a key role in Puritan American history and is famous for the 1692 Salem witch trials, where several local people were executed for supposedly practicing witchcraft. There are several Salem attractions related to this time in the town’s history. The Witch House was the residence of a trial judge.
The Peabody Essex Museum displays a large collection of art and artifacts from around the world, including local art as well as a substantial Asian collection that features a restored Qing-era Chinese house. Other area attractions include Nathanial Hawthorne’s birthplace, Canobie Lake Park, and the Bakers Island Lighthouse.
Cost:
$$ – Most museums and attractions have moderate entrance fees; dining and lodging options range from budget to boutique.Best time to visit:
- October – For Halloween-themed events, festivals, and tours.
- Spring and summer – For milder weather, museum visits, and fewer crowds.
Local tips:
Visit in late September or early November for a quieter version of Salem’s spooky charm. Book accommodations early if traveling in October—it’s the busiest time of year.How to Get to Salem:
Salem is accessible via MBTA commuter rail from Boston’s North Station or by car. There are also seasonal ferry services from Boston to Salem Harbor.Map & More Info:
Salem, MARomantic Places to Visit in Massachusetts:
5. Nantucket
Nantucket is an island located in the Atlantic Ocean about 14 miles south of Cape Cod. It is a popular summer destination for the affluent, and home values here are some of the highest in the US. The island features many examples of New England seaport architecture from the late 18th and early 19th centuries.
There are several beaches to relax on and lighthouses to explore. Other attractions include the Nantucket Whaling Museum, the Coskata-Coatue Wildlife Refuge, and the Maria Mitchell Association. Several small islands are located nearby, including the Muskeget and Tuckernuck islands, which can be reached by boats that depart from Nantucket Harbor.
Cost:
$$$ – Nantucket has some of the highest home values and vacation costs in the U.S., but it’s rich in charm, beauty, and exclusivity.Best time to visit:
- Late spring through early fall – June to September is ideal for beaches, sightseeing, and warm weather fun.
- September – A great time for fewer crowds with lingering summer charm.
Local tips:
Book ferry tickets well in advance, especially for cars. Bring a bike or rent a scooter to explore more of the island comfortably.How to Get to Nantucket:
Ferries depart regularly from Hyannis (on Cape Cod); flights also arrive from Boston, NYC, and other regional airports.Map & More Info:
Nantucket, MA6. Provincetown
Provincetown is a seaside town on the northern point of Cape Cod. The town is well known for being the site of the 1620 landing of the Mayflower. The landing site is commemorated with the Pilgrim Monument, while the nearby Provincetown Museum features exhibits related to the Pilgrims, the Mayflower voyage, and other local history.
The town has long been known as a safe haven for LGBT travelers and residents and is home to many artists. The lively Commercial Street is lined with art galleries, eateries, clubs, cabarets, and shopping. The Race Point Light is a historic lighthouse located in Provincetown that offers overnight accommodations in the Keeper’s House. Next read: Best Romantic Places to Stay in Provincetown
Cost:
$$–$$$ – Mid-range to upscale pricing for dining and lodging, especially during peak summer months and events.Best time to visit:
- June through September – For festivals, beach days, and vibrant town life.
- October – For quieter charm with lingering warmth and colorful foliage.
Local tips:
Book accommodations early—especially during Pride, Carnival Week, or summer weekends. Biking is a great way to get around the dunes and town without parking stress.How to Get to Provincetown:
Drive from Boston (about 2.5 hours), take the seasonal ferry from Boston to Provincetown Harbor, or fly into Provincetown Municipal Airport.Map & More Info:
Provincetown, MA7. Plymouth
Plymouth is a small town with big historical significance. This coastal town is the location of the first Pilgrim settlement and the oldest town in New England. Plymouth is a popular tourist destination during the Thanksgiving holiday season as it was the site of the first Thanksgiving feast.
Pilgrim Memorial State Park is home to a boulder that is claimed to be the place where the pilgrims first touched land. A replica of the original Mayflower, called The Mayflower II, is typically moored at the park. Plimoth Plantation, a popular family destination, is a living history museum with a recreation of the original settlement, craft activities, and several live animals.
Cost:
$–$$ – Budget-friendly for day trips and museum entry; lodging and restaurants offer a range of pricing options.Best time to visit:
- Fall – Especially during November to experience Thanksgiving-themed events and crisp coastal air.
- Spring/Summer – For pleasant walking weather, waterfront strolls, and fewer crowds.
Local tips:
Reserve ahead for Plimoth Plantation tours during holidays. Pair your visit with a seafood lunch along the harbor—many spots offer views of the Mayflower II.How to Get to Plymouth:
Accessible by car via Route 3 from Boston; commuter rail service is also available via the MBTA’s Kingston/Plymouth line.Map & More Info:
Plymouth, MAFamily-friendly Places to Visit in Massachusetts:
8. Amherst
Amherst is a college town in the Connecticut River valley and is home to two colleges and a university. Several famous people have lived in Amherst, including Emily Dickinson, whose birthplace and home is now a museum about her work and life. The Eric Carle Museum of Picture Books can also be found here and features children’s books from all over the world.
Rounding out the museum scene are the Beneski Museum of Natural History and the eclectic Mead Art Museum. Nearby Mount Norwottuck and Bare Mountain as well as Mount Holyoke Range State Park provide ample opportunities to explore the outdoors through hiking and other activities.
Cost:
$–$$ – Affordable dining and attractions; most museums have modest or suggested donations. Outdoor activities are free or low-cost.Best time to visit:
- Spring – For wildflowers, hiking, and campus events.
- Fall – For crisp weather and stunning New England foliage.
Local tips:
Plan time to walk through the Five College area (Amherst, Hampshire, Mount Holyoke, Smith, and UMass Amherst). Stop by a local café for student-friendly fare and literary ambiance.How to Get to Amherst:
Accessible by car from Boston (about 2 hours) or via bus service through Peter Pan and Megabus. Amtrak stops in nearby Northampton.Map & More Info:
Amherst, MA9. Worcester
Centrally located, Worcester is an easy drive from many of Massachusetts’ major cities. The town features several museums such as the Worchester Art Museum and the Worchester History Museum. For families, there is also an ecology museum called the EcoTarium, which features indoor and outdoor exhibits geared towards children. Visitors can relax and experience the outdoors at one of the several city and state parks nearby.
Salisbury Park features a 56-foot-high stone tower that looks like a castle and makes for an interesting visit. Indian Lake and the Wachusett Reservoir provide opportunities for fishing and boating during the warm months.
Cost:
$–$$ – Most attractions are budget-friendly or family-priced; parking is widely available and often free.Best time to visit:
- Spring/Summer – For fishing, boating, and park visits.
- Fall – For foliage walks and museum days.
Local tips:
Plan a mix of indoor and outdoor stops. For lunch, visit Shrewsbury Street—Worcester’s restaurant row. Families with kids should check EcoTarium’s special weekend programs.How to Get to Worcester:
Located just off I-290 and I-90. Also served by Amtrak, MBTA commuter rail (Worcester Line), and regional bus services.Map & More Info:
Worcester, MA10. Hyannis
Hyannis Main Street is a charming all-American Main Street in Hyannis, Massachusetts, commonly referred to as the capital of Cape Cod for its prime geographic location on the Mid-Cape. The town is best known as the home of Barnstable Municipal Airport, which serves as a major transportation hub for most of the rest of Cape Cod and nearby destinations such as Martha's Vineyard. A wide array of quaint restaurants, cafes, and shops line the town's Main Street, ranging from beachfront favorites such as ice cream parlors and surf shops to fine dining establishments in a variety of international cuisine styles. The JFK Hyannis Museum explores the region's connection to United States President John F. Kennedy, while Bismore Memorial Park, located on adjacent Ocean Street, is home to an Art Shanties colony of artisan vendors. More Hyannis beaches
Cost:
$$ – Accessible for most travelers, with a mix of casual and upscale dining and shopping options.Best time to visit:
- Late spring to early fall – Ideal for walking, shopping, and beach weather.
- Summer – For peak activity, island connections, and vibrant street life.
Local tips:
Parking can fill up fast in summer—arrive early or use one of the nearby lots. Don’t miss a sunset at the harbor or a scoop from a local creamery before heading out.How to Get to Hyannis:
Drive via Route 6, fly into Barnstable Municipal Airport, or take a ferry from Nantucket or Martha’s Vineyard. Bus service is available from Boston and Providence.Map & More Info:
Hyannis, MAPlan Your Trip