Your Road Trip Guide for Summer 2023
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
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 Beach.
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 evening.
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.