Places to Visit in Massachusetts

Location:

The Berkshires, Massachusetts (about 2.5 hours west of Boston)

Highlights:

Looking for rolling hills, charming towns, and a flourishing arts scene? The Berkshires deliver a perfect mix of nature, culture, and small-town charm in the heart of western Massachusetts.

Recommended For:

Fall foliage seekers, art lovers, music fans, outdoor adventurers, and anyone craving a scenic rural escape.

What I Love: ♥

A calendar full of festivals, live music at Tanglewood, and peaceful countryside trails that come alive with color in autumn and snow in winter.

• Explore Lenox, Williamstown, and other charming small towns dotted with farms, shops, and classic New England character.
• Enjoy live summer concerts by the Boston Symphony Orchestra at Tanglewood Music Center.
• Visit top cultural attractions like the Norman Rockwell Museum, Williamstown Theatre Festival, and MASS MoCA.
• Get outside with hiking, kayaking, rafting, fishing, or golfing during the warmer months.
• Embrace winter with skiing, snowshoeing, and snowboarding on snow-covered trails and slopes.

Cost:

$$–$$$ – Lodging and experiences range from boutique inns to luxurious resorts; museums and events may require ticketed admission.

Best time to visit:

• Fall – For jaw-dropping foliage displays.
• Summer – For music festivals, cultural events, and outdoor adventures.

Local tips:

Book lodging early for fall foliage season and summer festival weekends. Bring layers—weather can shift quickly in the hills.

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.

Map & More Info:

The Berkshires, MA

Location:

Cape Cod, Massachusetts (a peninsula extending into the Atlantic Ocean from the southeastern coast of the state)

Highlights:

Dreaming of windswept beaches, charming towns, and whale sightings? Cape Cod is a quintessential coastal retreat, perfect for outdoor lovers, romantics, and curious travelers alike.

Recommended For:

Nature lovers, families, couples, cyclists, and anyone looking to explore New England’s iconic seaside charm.

What I Love: ♥

Whale watching under spring skies, biking along scenic trails, browsing antique shops, and ending the day with a classic Cape Cod sunset.

• Stroll along sandy beaches and windswept dunes or catch the evening sky glowing over the Atlantic.
• Whale watch from spring to fall—March through October is prime time for spotting humpbacks and other majestic species.
• Hike forested trails, paddle around serene ponds, or cycle along the Cape Cod Rail Trail for breathtaking views and fresh ocean air.
• Explore cranberry bogs, a nod to Cape Cod’s agricultural heritage, especially vibrant during the fall harvest.
• Shop at local boutiques, antique stores, and quaint souvenir shops in towns full of New England history and charm.

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 and vibrant energy.

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, MA

Location:

Martha’s Vineyard, Massachusetts (an island south of Cape Cod)

Highlights:

Looking for a breezy island retreat filled with coastal charm? Martha’s Vineyard is a favorite summer escape for both celebrities and locals, known for its quiet beaches, boutique shops, and laid-back luxury.

Recommended For:

Couples, families, artists, and travelers seeking scenic relaxation, boutique shopping, and a dose of New England coastal elegance.

What I Love: ♥

The timeless feel of its harbor towns, serene beach walks, and cultural touches like local theater and film festivals that round out its peaceful island appeal.

• Relax on picturesque beaches and stroll through quaint towns surrounded by scenic island views.
• Shop at locally owned boutique shops offering hand-crafted souvenirs and upscale coastal finds.
• Visit the historic lighthouse on Chappaquiddick Island or take in a show at the Martha’s Vineyard Playhouse.
• Experience the island’s vibrant arts scene with weekly performances and a beloved annual film festival.
• Stay in charming inns or vacation homes—perfect for slow mornings, beach days, and sunset views.

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, MA

Location:

Salem, Massachusetts (about 30 minutes north of Boston)

Highlights:

Looking for haunted history and coastal charm? Salem is best known for its infamous 1692 witch trials, but it also offers rich literary heritage, global art, and seaside sights that go far beyond the spooky season.

Recommended For:

History buffs, Halloween lovers, literature fans, and curious travelers eager to explore one of New England’s most iconic historic towns.

What I Love: ♥

Immersive museums, well-preserved colonial architecture, and a cultural scene that blends folklore, fine art, and maritime legacy.

• Visit The Witch House, the home of a Salem witch trials judge, for a firsthand look into Puritan justice and 17th-century life.
• Learn about Salem’s dark past through multiple witch trial-themed museums and attractions located throughout the historic downtown.
• Explore the acclaimed Peabody Essex Museum, home to art and artifacts from around the world, including a restored Qing dynasty Chinese house.
• Tour literary landmarks like Nathaniel Hawthorne’s birthplace, and don’t miss coastal gems like the Bakers Island Lighthouse.
• Play at Canobie Lake Park, a nearby amusement park offering family-friendly fun just a short drive away.

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, MA

Romantic Places to Visit in Massachusetts:

Location:

Nantucket, Massachusetts (an island 14 miles south of Cape Cod in the Atlantic Ocean)

Highlights:

Looking for a luxury island escape with maritime charm? Nantucket is the definition of New England elegance—home to historic homes, windswept beaches, and one of the most storied seafaring histories in the U.S.

Recommended For:

Affluent travelers, history buffs, architecture lovers, beachgoers, and families seeking a peaceful yet upscale coastal destination.

What I Love: ♥

The blend of pristine beaches and historic whaling town ambiance, plus the island’s top-tier preservation of 18th- and 19th-century seaport architecture.

• Tour cobblestone streets lined with New England seaport architecture from the 18th and 19th centuries.
• Visit the Nantucket Whaling Museum to dive deep into the island’s maritime heritage.
• Relax on scenic beaches or explore historic lighthouses scattered across the island’s coastline.
• Explore the Coskata-Coatue Wildlife Refuge and the Maria Mitchell Association for a mix of natural beauty and science education.
• Venture to nearby Muskeget and Tuckernuck Islands via boat 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, MA

Location:

Provincetown, Massachusetts (at the northern tip of Cape Cod)

Highlights:

Looking for a destination with deep history, vibrant culture, and seaside flair? Provincetown is a welcoming, artistic community where the Mayflower first landed and creativity thrives year-round.

Recommended For:

LGBTQ+ travelers, artists, history lovers, beachgoers, and anyone seeking an inclusive, energetic coastal town with personality.

What I Love: ♥

A place where Pilgrim history meets rainbow flags, and art galleries blend seamlessly with ocean views and historic lighthouses.

• Visit the Pilgrim Monument and Provincetown Museum to explore the 1620 Mayflower landing and the town’s colonial roots.
• Experience one of the country’s most enduring LGBTQ+ friendly destinations and enjoy the vibrant artist community.
• Stroll down Commercial Street, filled with art galleries, eateries, clubs, cabarets, and boutique shopping.
• Stay overnight at the Race Point Light—a scenic lighthouse offering rare accommodations in the Keeper’s House.
• Enjoy whale-watching tours, stunning dunes, and peaceful bike rides on the Province Lands Trail.

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, MA

Location:

Plymouth, Massachusetts (about 45 minutes south of Boston, on the South Shore)

Highlights:

Want to walk where American history began? Plymouth is the birthplace of New England, home of the first Pilgrim settlement and the legendary first Thanksgiving—offering a rich blend of living history and coastal charm.

Recommended For:

Families, history lovers, cultural travelers, and those seeking meaningful experiences around Thanksgiving and beyond.

What I Love: ♥

Stepping back in time at Plimoth Plantation, walking the historic waterfront, and seeing where the Pilgrims first set foot on American soil.

• Visit Pilgrim Memorial State Park, home to the iconic Plymouth Rock, a boulder marking the traditional landing site of the Pilgrims.
• See the Mayflower II, a full-scale replica of the original ship, typically docked at the park’s waterfront.
• Explore Plimoth Plantation, a living history museum featuring a full-scale recreation of the 17th-century village, complete with costumed interpreters, craft demonstrations, and heritage livestock.
• Celebrate Thanksgiving where it all began—Plymouth hosts special events, reenactments, and feasts every November.

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, MA

Family-friendly Places to Visit in Massachusetts:

Location:

Amherst, Massachusetts (in the Connecticut River Valley of western Massachusetts)

Highlights:

Looking for a mix of intellectual energy and natural beauty? Amherst is a quintessential college town packed with world-class museums, literary history, and scenic hiking trails in every direction.

Recommended For:

Literature lovers, museum-goers, families, students, and outdoor enthusiasts looking for a vibrant yet peaceful getaway.

What I Love: ♥

Thoughtful museums, the legacy of Emily Dickinson, and nearby mountain trails that pair perfectly with a weekend of cultural exploration.

• Explore Emily Dickinson’s birthplace and home, now a museum dedicated to her life and literary contributions.
• Visit The Eric Carle Museum of Picture Book Art, a colorful celebration of global children’s literature and illustration.
• Learn at the Beneski Museum of Natural History, where fossils, minerals, and dinosaur tracks captivate curious minds of all ages.
• Admire art at the Mead Art Museum, located on the Amherst College campus with a unique and rotating art collection.
• Hike local gems like Mount Norwottuck, Bare Mountain, and the Mount Holyoke Range State Park for panoramic views and fresh air.

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, MA

Location:

Worcester, Massachusetts (centrally located, easily accessible from Boston, Springfield, and Providence)

Highlights:

Want a cultural and kid-friendly escape without leaving central Massachusetts? Worcester is packed with hands-on museums, peaceful parks, and historic landmarks—making it an underrated gem for day trips and weekend getaways.

Recommended For:

Families, art lovers, history buffs, and outdoor enthusiasts looking for an affordable, centrally located destination.

What I Love: ♥

From art and science museums to castle-like towers and fishing lakes, Worcester surprises with variety and charm in every season.

• Discover the Worcester Art Museum, home to a diverse global collection from ancient to contemporary art.
• Learn local stories at the Worcester History Museum, which dives into the city’s rich industrial and civic past.
• Bring the kids to the EcoTarium, a hands-on science and ecology museum with both indoor and outdoor exhibits for curious young minds.
• Visit Salisbury Park, home to a 56-foot stone with panoramic views and photo-worthy architecture.
• Relax or cast a line at Indian Lake and Wachusett Reservoir, both offering boating and fishing in warmer 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, MA

Location:

Hyannis, Massachusetts (on the Mid-Cape, often called the capital of Cape Cod)

Highlights:

Want classic Cape Cod charm with a walkable downtown and seaside energy? Hyannis is the Mid-Cape hub, known for shopping, beaches, and a deep connection to the Kennedy legacy.

Recommended For:

Families, beach lovers, shoppers, day-trippers, and anyone seeking a Cape Cod experience that mixes local flavor with historic charm.

What I Love: ♥

Strolling Main Street, exploring JFK’s history, catching a ferry to the islands, and grabbing a cone from a classic seaside ice cream stand.

• Walk Hyannis Main Street, a lively stretch of shops, cafés, surf stores, and ice cream parlors with a cozy small-town feel.
• Dine at beachside spots or explore international cuisines in elegant restaurants along the street.
• Visit the JFK Hyannis Museum to explore the town’s connection to President John F. Kennedy and the iconic Kennedy family compound.
• Browse local art at Bismore Memorial Park, where the Art Shanties colony features rotating artisan vendor stalls.
• Fly or ferry—Hyannis is home to Barnstable Municipal Airport and ferry service to Martha’s Vineyard and Nantucket, making it a perfect base for island-hopping.

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, MA