Scenic view of Martha's Vineyard. The 2010 census shows that 16,535 residents call Martha's Vineyard home.

8 Ideal Destinations For A 3-Day Weekend In Massachusetts

Experience an unforgettable three-day weekend getaway in Massachusetts, filled with diverse destinations. Embrace the charm of Cape Cod. Explore picturesque towns like Provincetown, relax on beautiful beaches, and enjoy fresh seafood. Take a journey to Martha’s Vineyard, where fascinating history meets vibrant culture. Visit the beautiful Oak Bluffs, explore the serene beaches, and stroll through charming streets. In  Massachusetts, you will find a perfect blend of coastal beauty, captivating history, and urban excitement for a memorable three-day weekend.

Martha’s Vineyard

Carpenter Gothic Cottages with Victorian style, gingerbread trim on Lake Avenue, Oak Bluffs on Martha's Vineyard, via Wangkun Jia / Shutterstock.com
Carpenter Gothic Cottages with Victorian style, gingerbread trim on Lake Avenue, Oak Bluffs on Martha's Vineyard, via Wangkun Jia / Shutterstock.com

A captivating island where dreams come alive, Martha’s Vineyard is an exhilarating voyage for visitors looking to enjoy serenity. Day one, explore the picturesque streets of Edgartown, adorned with historic homes and quaint boutiques. On day two, embrace the island’s natural wonders. Bask in the sun’s warm embrace on South Beach’s golden sands, the rhythmic waves serenading your senses. Traverse vibrant trails, embracing the scenic beauty of Polly Hill Arboretum. Day three, embrace the island’s cultural tapestry. Discover the rich arts scene in Oak Bluffs, adorned with whimsical gingerbread cottages. Unwind with a sunset sail, the sky painting a masterpiece of hues. In the end, Martha’s Vineyard awaits your embrace.

Nantucket

Traditional New England buildings and stores on Nantucket Island in Massachusetts, via EQRoy / Shutterstock.com
Traditional New England buildings and stores on Nantucket Island in Massachusetts, via EQRoy / Shutterstock.com

Embark on a whirlwind adventure to Nantucket, where captivating sights and oceanic wonders await. Off the coast of Cape Cod, visitors can traverse cobblestone streets and admire historic homes and the Whaling Museum’s fascinating tales. Savor seafood delicacies at harborside restaurants, gazing at the sun-kissed waves. On day two, bask in the island’s natural beauty. Stroll along pristine beaches and dip your toes in the refreshing surf—cycle through idyllic landscapes, glimpsing lighthouses like the Brant Point Lighthouse standing tall. Set sail on a thrilling whale-watching excursion, witnessing majestic creatures breach the cerulean waters. Explore charming boutiques and acquire unique treasures on this magical escape. Let the memories of Nantucket ignite a desire to return to this coastal haven.

Cape Cod

Nauset Beach, Cape Cod, Eastham, via Jerry Callaghan / Shutterstock.com
Nauset Beach, Cape Cod, Eastham, via Jerry Callaghan / Shutterstock.com

Where coastal magic and endless adventures beckon, Cape Cod awaits visitors on the peninsula’s northern side. On day one, enjoy the sandy shores of Coast Guard Beach in Eastham, where visitors can swim, surf, and relax. Discover the vibrant charm of Provincetown, adorned with colorful art galleries and a lively LGBTQ+ scene. On day two, pedal along the scenic 22-mile-long Cape Cod Rail Trail, passing through picturesque towns and verdant landscapes. Savor the day’s catch at a quaint seafood shack or enjoy the Cape Cod National Seashore, immersing yourself in its beauty and dune-studded shores. Enjoy Cape Cod, where coastal bliss lingers long after the journey ends.

Ocean Edge Resort and Golf Club

Ocean Edge Resort and Golf Club in Cape Cod, via
Ocean Edge Resort and Golf Club in Cape Cod, via Ocean Edge Resort and Golf Club (capecodchamber.org)

Escape to a realm of luxury and tranquility at Ocean Edge Resort and Golf Club in Brewster, Massachusetts. On day one, indulge in the resort’s abundant amenities, from the pool, spa, and golf course. Tee off at the Nicklaus-designed golf course, perfecting your swing amidst breathtaking views. Day two, surrender to the serenity of the private beach, sinking your toes into soft sand and listening to the gentle lull of ocean waves. Immerse yourself in rejuvenating spa treatments, releasing all tensions. Day three, savor delectable cuisine at the resort’s fine dining establishments, sipping on crafted cocktails as the sun sets. Ocean Edge, where days of luxury blend seamlessly with moments of pure bliss, awaits your arrival.

Wequassett Resort and Golf Club

Wequassett Resort in Massachusetts, via
Wequassett Resort in Massachusetts, via Cape Cod Activities and Experiences | Wequassett

An extraordinary retreat located in Harwich, Massachusetts, on Cape Cod, Wequassett Resort and Golf Club is where paradise awaits. On day one, indulge in the resort’s lavish amenities. Lounge by the pool, immersed in luxury and serenity. Tee off at the championship golf course, surrounded by picturesque landscapes. On day two, succumb to the allure of the private beach, sinking your feet into powdery sands and surrendering to the rhythm of the ocean. Pamper yourself with revitalizing spa treatments, restoring your mind, body, and soul. Day three, delight in culinary delights at the resort’s renowned restaurants, savoring gourmet creations as the sun paints the sky in vibrant hues—Wequassett is where timeless elegance and unrivaled beauty merge.

Lenox

The Mount, home of American author Edith Wharton, seen from the formal French flower garden, via LEE SNIDER PHOTO IMAGES / Shutterstock.com
The Mount, home of American author Edith Wharton, seen from the formal French flower garden, via LEE SNIDER PHOTO IMAGES / Shutterstock.com

Come to Lenox, Massachusetts, to experience a perfect blend of peace and culture. On the first day, enjoy an outdoor concert in the beautiful Berkshire Hills at Tanglewood, and stroll through the lively streets to browse the charming boutiques and art galleries. On the second day, take a scenic hike through Kennedy Park and enjoy the stunning views. Explore the Massachusetts Museum of Contemporary Art (MASS MoCA) to learn about the region’s artistic history. On the third day, visit The Mount, Edith Wharton’s former estate, and enjoy a picnic in the peaceful gardens. Lenox is a sanctuary where you can find tranquility and culture in harmony. Come and experience it for yourself.

Falmouth

Falmouth Harbor is located on the south side of Cape Cod halfway between Newport, RI and Nantucket Island
Falmouth Harbor is located on the south side of Cape Cod halfway between Newport, RI and Nantucket Island

Take a coastal escape to Falmouth, Massachusetts, where tranquility meets seaside charm. Thrust yourself into exploring the town’s coastal beauty by strolling along the picturesque shores of Old Silver Beach. Explore the quaint streets of Falmouth Village, perusing unique boutiques and savoring fresh seafood delights. On day two, embrace outdoor adventures on the Shining Sea Bikeway, cycling through scenic landscapes and enjoying panoramic views of the ocean. Discover the rich maritime history at the Woods Hole Oceanographic Institution. Day three, embark on a relaxing ferry ride to Martha’s Vineyard, exploring the island’s enchanting towns and serene beaches—Falmouth, where coastal bliss and New England charm intertwine, beckons you to embrace its allure.

Provincetown

View of beach in Provincetown, Massachusetts with beautiful blue sky
View of beach in Provincetown, Massachusetts with beautiful blue sky

Provincetown, Massachusetts,  is located at the tip of Cape Cod and approximately 120 miles southeast of Boston, where art, culture, and coastal beauty converge. Become immersed in the town’s artistic energy. Explore the renowned art galleries and studios, admiring the diverse works that captivate the senses—delight in the lively atmosphere of Commercial Street, filled with boutique shops and unique eateries. On day two, wander along the scenic trails of the Cape Cod National Seashore, basking in the beauty of dunes and pristine beaches. Take a whale-watching excursion, marveling at majestic creatures in their oceanic realm. Day three, revel in Provincetown’s LGBTQ+ scene, celebrating diversity and inclusivity. Experience vibrant nightlife and join in festive events.

Whether you seek coastal bliss, historic charm, or urban excitement, Massachusetts has it all for a memorable three-day weekend. From the sandy shores of Cape Cod to the intriguing history of Falmouth and the vibrant streets of Provincetown, each destination offers a unique and captivating experience. Immerse yourself in the rich culture, indulge in culinary delights, and explore scenic landscapes. Massachusetts is the perfect getaway for a diverse and unforgettable weekend escape.

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