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Massachusetts Travel Guide

The ultimate guide to the best things to do and see in Massachusetts – with LGBTQ travel tips

Boston Travel Guide

Welcome to Massachusetts, a state where history meets innovation, and diversity thrives around every corner. Whether you identify as LGBTQ+ or are a proud millennial traveler seeking adventure, culture, and memorable experiences, Massachusetts has it all.

From the bustling streets of Boston to the serene landscapes of Cape Cod, this guide is your key to unlocking the best of the Bay State.

Rockport harbor

Allegedly one of the most photographed harbors in Massachusetts. Very romantic, no?

When to Visit Massachusetts

The best times to visit Massachusetts depend on your preferences and the type of experiences you seek.

Spring (March to May): Massachusetts awakens with the vibrant colors of spring during this time. As flowers bloom and temperatures gradually rise, it’s the perfect season for outdoor activities such as hiking, biking, and exploring the state’s numerous parks and gardens. One highlight of spring is the iconic Boston Marathon, typically held in April, which attracts participants and spectators from around the world.

Summer (June to August): Summer is the peak tourist season in Massachusetts, particularly in coastal regions like Cape Cod and Martha’s Vineyard. With warm temperatures and sunny days, it’s ideal for beachgoers, water sports enthusiasts, and sunseekers. The season is also packed with festivals, outdoor concerts, and various events, making it a lively and bustling time to visit.

Fall (September to November): Massachusetts truly shines during the fall season when the foliage transforms into a breathtaking tapestry of red, orange, and gold. The natural beauty is complemented by activities like apple picking, visits to pumpkin patches, and navigating corn mazes. The pleasant weather in the fall is perfect for outdoor adventures, scenic drives, and capturing Instagram-worthy moments.

Winter (December to February): Winter in Massachusetts brings cold temperatures and ample snowfall, especially in the western and mountainous regions. For winter sports enthusiasts, it’s a fantastic time to hit the slopes for skiing, snowboarding, and ice skating. The holiday season also adds a special charm to cities like Boston, with festive decorations, seasonal markets, and events.

live lobster

Lobster—it’s what’s for dinner in Massachusetts :)

Shoulder Seasons (Late spring and early fall): Late spring (May) and early fall (September to October) offer the best of both worlds. These shoulder seasons provide pleasant weather, fewer crowds, and more affordable accommodation prices. It’s an excellent time to engage in sightseeing, explore historic sites, and enjoy outdoor activities without the bustling summer crowds.

Ultimately, the timing of your visit to Massachusetts should align with your interests and desired experiences. Whether you prefer the warmth of summer, the kaleidoscope of fall foliage, or the tranquility of the shoulder seasons, the Bay State has something to offer year-round. Consider specific events and festivals that may influence your travel plans and enhance your overall experience.

Boston Charlesmark

Massachusetts Travel Itinerary

Here’s a suggested one-week itinerary for exploring the diverse attractions and regions of Massachusetts:

Day 1: Arrival in Boston — Begin your journey in historic Boston. Explore the charming neighborhoods of Beacon Hill and the North End, absorbing the city’s rich history and architecture. Wander along the Freedom Trail, immersing yourself in America’s past, and savor a seafood dinner by the waterfront.

Day 2: Visit Boston — Dive deeper into Boston’s cultural scene. Spend your morning at the Museum of Fine Arts or the Isabella Stewart Gardner Museum, then follow the Harborwalk through the dynamic Seaport District. Discover art galleries and boutique shops in the trendy South End before indulging in a diverse culinary experience in Back Bay.

Salem, MA

Day 3: Day Trip to Salem — Embark on a day trip to Salem, famous for its witch trials history. Explore the Salem Witch Museum and the historic waterfront. Unwind amid unique shops and cafes, then return to Boston for the night.

Day 4: Visit Cape Cod — Journey to Cape Cod, a paradise of beaches and charming towns. Spend the day in Hyannis or Falmouth, embracing the coastal atmosphere, shopping, and dining. Consider a ferry ride to Martha’s Vineyard or Nantucket.

Day 5: Explore Cape Cod Beaches — Explore more of Cape Cod, making your way to Provincetown at the Cape’s tip. Delve into Provincetown’s LGBTQ+ history, vibrant arts scene, and welcoming ambiance. Relish fresh seafood in a picturesque waterfront setting.

Cape Cod - Provincetown Beach

Day 6: Plymouth and Cape Cod National Seashore — Head to Plymouth, where the Pilgrims landed. Visit Plymouth Rock, the Mayflower II, and Plimoth Plantation Museum. Later, explore Cape Cod National Seashore, with opportunities for hiking and beachcombing.

Day 7: Visit the North Shore — Venture to the North Shore, discovering the coastal towns of Rockport and Gloucester. Explore the Salem Maritime National Historic Site, an ode to maritime history. Depending on your departure time, squeeze in last-minute shopping or dining in Boston before heading home.

This one-week itinerary offers a diverse experience of Massachusetts, combining its historical treasures, captivating coastal regions, and lively cultural offerings. Feel free to customize it to your interests and the season of your visit. Massachusetts promises an array of options for additional day trips, outdoor adventures, and cultural explorations to ensure a memorable journey.

LGBTQ – Massachusetts Gay Travel Guide

Massachusetts has a rich history of LGBTQ+ activism and a welcoming atmosphere for travelers of all backgrounds. It was the first state to recognize marriage equality.

Whether you identify as LGBTQ+ or an ally, this gay travel guide will help you navigate the Bay State’s inclusive and vibrant scene. Here are three must-visit LGBTQ+ friendly places in Massachusetts:

1. Provincetown (Cape Cod)

Provincetown, affectionately known as “P-Town,” is a top LGBTQ+ destination and a true haven for all. Located at the tip of Cape Cod, it’s renowned for its LGBTQ+ history, diverse community, and artistic spirit. In Ptown, you can visit the Provincetown Pride in June, a lively celebration of LGBTQ+ culture, or explore the Provincetown Art Association and Museum, which features an extensive collection of LGBTQ+ art. Stroll along Commercial Street to discover LGBTQ+-owned shops, restaurants, and bars. Don’t forget to catch a show at the Crown & Anchor, a renowned venue for drag performances and live entertainment.

2. Northampton (The Pioneer Valley)

Known as the “Lesbian Capital of the World,” Northampton is a welcoming and inclusive city in western Massachusetts. Start your visit at Paradise City, a charming downtown area filled with LGBTQ+-friendly shops and cafes. Explore the LGBTQ+ history of the area by visiting the LGBTQ+ Archives at UMass Amherst, where you can learn about the region’s vibrant queer past. The Northampton Pride Parade and Festival in May is a colorful and spirited event that celebrates diversity and inclusion.

3. Boston

Boston, the state capital, boasts a thriving LGBTQ+ scene with a range of events, bars, and organizations. Begin your exploration in the South End, a historic LGBTQ+-friendly neighborhood known for its art galleries, shops, and vibrant dining scene. Attend Boston Pride in June, which includes a Pride Parade and Festival. For a night out, head to Club Cafe or Jacques Cabaret for lively drag performances and entertainment.

Remember, Massachusetts offers a welcoming atmosphere year-round, but LGBTQ+ events and celebrations often take place in June during Pride Month.

Regardless of when you visit, you’ll find a state that celebrates diversity and offers a warm embrace to all travelers. Explore, connect, and make unforgettable memories in LGBTQ+ Massachusetts.

Massachusetts Travel Blogs

Somerville, MA— Somerville is home to a lot of quirky things, but nothing as bright and loud as the annual Honk! Festival. It’s billed as a festival of activist street bands, with everything from grandmas in neon orange feather hats, to children singing along to popular marching tunes. Across the country and around the world, a new …

Read More about Bright colors and loud noises: The Honk Festival