Your Road Trip Guide through the Eastern Shore of MA

by Abbey

Embarking on a road trip through Eastern Massachusetts is an unforgettable adventure that promises a delightful blend of history, scenic beauty, and vibrant city life. From the cobblestone streets of Boston, steeped in revolutionary heritage, to the idyllic coastal towns that dot the picturesque Cape Cod shoreline, this region captivates travelers with its rich cultural tapestry and diverse landscapes. Whether you seek the thrill of exploring charming villages, savoring fresh seafood delicacies, or immersing yourself in the beauty of nature, a road trip through the Eastern Coast of New England offers an enticing array of experiences that will leave you with cherished memories. We did the heavy lifting so you don't miss a single thing during your drive. So buckle up, hit the open road, and let the wonders unfold before your eyes.



Cape Cod National Seashore: Explore the stunning coastline of Cape Cod National Seashore, which stretches for 40 miles and offers scenic beaches, sand dunes, and nature trails. Don't miss popular spots like Coast Guard Beach, Marconi Beach, and Race Point Beac

Chatham: Visit the charming town of Chatham, known for its picturesque Main Street lined with boutique shops, art galleries, and restaurants. Enjoy a stroll along Lighthouse Beach or take a seal-watching cruise from the harbor.

Provincetown: Head to the tip of Cape Cod and spend some time in Provincetown. Explore the vibrant art scene, walk along Commercial Street filled with shops and eateries, and visit the iconic Pilgrim Monument for panoramic views of the area.

Martha's Vineyard: Take a ferry from Woods Hole to Martha's Vineyard, a beautiful island off Cape Cod. Discover quaint villages, sandy beaches, and scenic bike trails. Don't miss visiting the towns of Oak Bluffs, Edgartown, and Aquinnah.

Nantucket: Another island worth exploring, Nantucket offers a unique blend of history and natural beauty. Stroll through cobblestone streets, admire the well-preserved historic homes, and enjoy the island's pristine beaches and charming lighthouses.

Sandwich: Visit the oldest town on Cape Cod, Sandwich, and explore its rich history. Take a tour of the Heritage Museums and Gardens, walk along the Sandwich Boardwalk, and visit the Sandwich Glass Museum to learn about the town's glass-making heritage.

Cape Cod Rail Trail: Embark on a biking adventure along the Cape Cod Rail Trail, a 22-mile paved trail that passes through several Cape Cod towns. Enjoy scenic views, stop at charming towns along the way, and take breaks at local cafes and ice cream shops.

Whale Watching: Cape Cod offers excellent opportunities for whale watching. Join a guided tour from towns like Provincetown or Barnstable and witness the majestic humpback whales, finback whales, and other marine life.

Wellfleet Drive-In Theater: Experience a classic drive-in movie night at the Wellfleet Drive-In Theater. Enjoy a double feature under the stars and grab some snacks from the concession stand for a nostalgic evenin

Cape Cod Wineries: Explore the Cape's wineries and vineyards. Take a wine tour, sample locally produced wines, and enjoy the picturesque surroundings. Some popular wineries include Truro Vineyards, Cape Cod Winery, and First Crush Winery.


Newport, Rhode Island: Start your South Coast road trip in Newport, known for its historic mansions, scenic waterfront, and vibrant atmosphere. Take a tour of the famous Newport Mansions, visit the picturesque Cliff Walk, and explore the charming shops and restaurants along Thames Street.

Block Island, Rhode Island: Take a ferry from Point Judith or Newport to Block Island, a beautiful island off the coast of Rhode Island. Enjoy the island's stunning beaches, go hiking or biking along the scenic trails, and visit the iconic Southeast Light.

Mystic, Connecticut: Head to Mystic, a charming coastal town known for its maritime history. Visit the Mystic Seaport Museum, where you can explore historic ships and learn about the region's maritime heritage. Don't miss the Mystic Aquarium, home to a variety of marine animals.

Watch Hill, Rhode Island: Visit Watch Hill, a picturesque village in Rhode Island. Relax on the beautiful sandy beaches, take a stroll along the Watch Hill Harbor, and enjoy panoramic views from the iconic Watch Hill Lighthouse.

New Bedford, Massachusetts: Explore the historic city of New Bedford, famous for its whaling history. Visit the New Bedford Whaling Museum to learn about the city's maritime past, explore the cobblestone streets of the Whaling National Historic Park, and enjoy fresh seafood at local restaurants.

Westport, Massachusetts: Visit Westport, a coastal town known for its beautiful beaches and nature reserves. Spend a day relaxing on Horseneck Beach, go birdwatching at Allens Pond Wildlife Sanctuary, or enjoy kayaking on the Westport River.


Plymouth: Begin your South Shore road trip in Plymouth, known as "America's Hometown." Visit Plymouth Rock, the iconic symbol of the arrival of the Pilgrims, and explore Plimoth Patuxet, a living history museum that recreates the Pilgrim settlement. Don't miss a visit to the Mayflower II, a replica of the ship that brought the Pilgrims to Americ

Duxbury Beach: Head to Duxbury and enjoy a day at Duxbury Beach. This beautiful sandy beach offers scenic views of the Atlantic Ocean, dunes, and coastal marshes. Take a walk along the beach, swim in the ocean, or have a picnic with the picturesque backdrop.

Scituate Lighthouse: Drive to Scituate and visit the Scituate Lighthouse, situated on Cedar Point. Take in the breathtaking views of the Atlantic Ocean, explore the surrounding beaches, and stroll along the Scituate Harbor, lined with shops and restaurants.

Nantasket Beach: Explore Nantasket Beach in Hull, a popular summer destination on the South Shore. Enjoy miles of sandy shoreline, go for a swim, and take a walk along the picturesque promenade. You can also visit Paragon Carousel, a historic carousel located near the beach.

Hingham: Discover the charming town of Hingham, known for its picturesque New England charm. Take a stroll along Hingham Harbor, visit the Old Ship Church, and explore the unique shops and restaurants in downtown Hingham.

Cohasset: Visit Cohasset, a beautiful coastal town known for its stunning beaches and historic sites. Explore Sandy Beach, visit the picturesque Cohasset Harbor, and take a walk through the quaint village center with its charming shops and restaurants.

Marshfield: Spend some time in Marshfield, known for its picturesque coastal scenery. Enjoy a day at Rexhame Beach or Green Harbor Beach, visit the Daniel Webster Wildlife Sanctuary, or explore the historic Winslow House

South Shore Plaza: If you're in the mood for shopping, make a stop at the South Shore Plaza in Braintree. This large shopping center offers a wide range of stores, restaurants, and entertainment options.

Blue Hills Reservation: Just north of the South Shore, you'll find the Blue Hills Reservation, a beautiful nature reserve with miles of hiking trails, scenic views, and recreational activities. Enjoy hiking to the summit of Great Blue Hill, visit the Blue Hills Trailside Museum, or have a picnic in one of the designated areas.


Freedom Trail: Embark on a historic journey by walking the Freedom Trail. This 2.5-mile trail takes you through 16 significant sites, including the Massachusetts State House, Paul Revere's House, and the Old North Church, offering a glimpse into Boston's rich history.

Cape Ann: Take a drive to Cape Ann, located just north of Boston. Explore the picturesque towns of Gloucester and Rockport, known for their charming harbors, art galleries, and scenic coastal landscapes. Don't miss visiting Halibut Point State Park and the iconic Motif No. 1.

Salem: Visit the historic city of Salem, famous for the Salem Witch Trials. Tour the Salem Witch Museum, explore the House of the Seven Gables, and wander through the charming streets lined with boutiques, restaurants, and historic landmarks.

Harvard University and Cambridge: Cross the Charles River and explore the vibrant city of Cambridge. Take a walk through Harvard Yard, visit the renowned Harvard University campus, and explore the lively Harvard Square filled with bookstores, cafes, and street performers.

North Shore Beaches: Enjoy a day at the beach by heading to the North Shore. Visit popular beach destinations like Revere Beach, Crane Beach in Ipswich, or Singing Beach in Manchester-by-the-Sea. Relax on the sandy shores and soak up the coastal beauty.

Lexington and Concord: Journey to the historic towns of Lexington and Concord, where the first battles of the American Revolution took place. Explore sites like the Lexington Battle Green, Minuteman National Historical Park, and the Old North Bridge, and learn about the birth of American independence.

Boston Harbor Islands: Take a ferry from downtown Boston and explore the Boston Harbor Islands. Visit Spectacle Island or Georges Island, where you can enjoy hiking trails, picnicking, and stunning views of the Boston skyline.

Fenway Park and Beacon Hill: Catch a baseball game at Fenway Park, home of the Boston Red Sox. Afterward, explore the charming Beacon Hill neighborhood, known for its historic brownstones, gaslit streets, and boutique shops. Don't miss a visit to the Massachusetts State House.

South End and SoWa: Discover the trendy South End neighborhood, known for its vibrant arts scene and trendy restaurants. Visit the SoWa Open Market, which features local artisans, food trucks, and a farmer's market on weekends.

Boston Common and Public Garden: Begin your exploration of Boston with a visit to the historic Boston Common, the oldest public park in the United States. Take a leisurely stroll through the adjacent Public Garden, known for its iconic swan boats and beautiful floral displays.

Now that you have all the sites to see, hop in your car and take on the open road! Whatever cities, areas and monuments you want to hit, you can do so on this New England adventure. Need a place to sleep as you work your way up the coast? Reach out to our rental department at and turn your road trip into a get-away.