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New England has long been a paradise for boaters, with its mix of historic harbors, rugged coastlines and picturesque seaside villages. While places like Newport and Martha’s Vineyard often steal the spotlight, there’s a world of lesser-known anchorages, charming waterfront towns and must-see maritime festivals waiting to be discovered. Whether you’re planning a leisurely cruise through Long Island Sound or an extended voyage along the rocky coast of Maine, here are some must-visit destinations and events that showcase the best of New England.
For boaters entering Long Island Sound, Connecticut’s coastline offers an appealing mix of history and scenery. While Mystic draws plenty of visitors to its famed Seaport Museum and Charles W. Morgan whaling ship, nearby Noank is a quieter alternative. For boaters entering Long Island Sound, Noank offers a more authentic taste of New England’s seafaring past.
A fun way to explore Noank from the water is with Tiki Bar Cruises, where you can sip cocktails on a floating tiki bar while soaking in the coastal scenery. On land, a stroll through the village reveals a tight-knit maritime community, with the Noank Historical Society offering insights into its shipbuilding heritage. For a great meal with waterfront views, Ford’s Black & Blue serves up fresh seafood and steaks in a relaxed setting. Dock at Noank Village Boatyard and enjoy Noank, the hidden gem that captures the charm of Connecticut’s shoreline.
Further west, the Connecticut River offers one of the most scenic detours in the region. Essex is a favorite stop, with its classic colonial architecture and the charming Connecticut River Museum, which brings the area’s maritime history to life. For a peaceful overnight anchorage, head upriver to Hamburg Cove, a tree-lined retreat with calm waters and an easygoing atmosphere. The marinas provide convenient access to the village’s shops, restaurants and historic charm, all just a short stroll away.
Rhode Island’s reputation as the “Ocean State” is well-earned. Newport is a vibrant coastal destination known for its historic mansions and sailing culture, but those looking for a more low-key stop should consider Wickford Village, a historic gem with well-preserved colonial homes, waterfront boutiques and excellent natural harbor. Across the bay, Dutch Harbor on Jamestown offers a laid-back alternative to Newport, with great sunset views and a relaxed marina scene at Conanicut Marina.
For those venturing offshore, Block Island is a must. Although the Great Salt Pond is the island’s most popular anchorage, consider anchoring near Crescent Beach for a quieter and more scenic experience. A bike ride to the Mohegan Bluffs rewards visitors with sweeping ocean views and a secluded stretch of sand that feels worlds away. If you’re boating from the mainland, Champlin’s Marina & Resort on Block Island provides great access points to the island and nearby attractions.
Massachusetts’ coastline blends maritime tradition with breathtaking scenery. While Martha’s Vineyard and Nantucket are popular island escapes, Cuttyhunk Island offers a far more tranquil experience. For boaters seeking a peaceful retreat, Cuttyhunk Island offers unspoiled beauty and a laid-back maritime charm. Dock at Cuttyhunk Marina, a welcoming harbor with moorings and slips, then cruise past Gosnold Harbor, where harbor seals bask on the rocks.
On shore, explore the island’s quiet village, enjoy a meal at The Cuttyhunk Picnic Co., where you can pick up delicious to-go boxes packed with fresh, locally sourced fare or grab fresh oysters from the Cuttyhunk Raw Bar, conveniently located at the fishing dock.
Perched on the shores of Buzzards Bay, Padanaram is a charming harbor village with a rich shipbuilding past. Its walkable center is home to locally owned shops, cozy cafés and beautifully preserved homes. Nearby, Apponagansett Park and Knowles Reserve offer scenic spots to stretch your legs. Boaters can dock at South Wharf Yacht Yard, which accommodates vessels up to 150 feet, making it a great stop to soak in this quiet coastal retreat.
Further up the coast, Wellfleet Harbor on Cape Cod is a haven for seafood lovers, known for its famous oysters and quiet, scenic mooring fields. The nearby Great Island Trail is one of the most rewarding hikes in the region with sweeping views of salt marshes and dunes. Gloucester is an essential stop if you’re looking for a working fishing town with deep maritime roots. Dock at Cape Ann Marina, explore the Man at the Wheel statue, and enjoy a seafood feast at Yella on the Water.
New Hampshire’s short stretch of coastline packs a punch. New Castle, just outside Portsmouth, is a charming spot with historic forts, scenic waterfront paths, and easy access to the vibrant downtown area. A few miles offshore, Gosport Harbor in the Isles of Shoals offers one of New England’s most unique boating destinations. While there are no docks or moorings for public use, it’s an easy day trip for boaters. The history of these remote islands dates back to the 1600s, and today, visitors can explore the hauntingly beautiful remnants of the Star Island retreat.
Maine’s rugged coastline is a boater’s dream, offering everything from bustling port cities to hidden coves. While Portland’s Old Port District is well worth a visit — especially for a meal at Eventide Oyster Co. — the real magic lies in the smaller harbors along the coast.
South Freeport is a great first stop, home to the iconic Harraseeket Lunch & Lobster Company and a peaceful harbor perfect for a quiet night on the water. Further east, Harpswell is a hidden gem with winding peninsulas, quaint fishing villages, and the one-of-a-kind Bailey Island Bridge, built entirely from granite. The town of Cundy’s Harbor offers a postcard-perfect setting, complete with working lobster boats and a fantastic seafood shack, Holbrook’s Wharf.
For those heading Down East, Stonington on Deer Isle is one of Maine’s best-kept secrets. This working fishing town has a rugged charm that feels like stepping back in time. From here, boaters can explore the stunning Merchant Row, an island-studded waterway with breathtaking views. Along the way, be sure to spot the distinctive Pumpkin House Lighthouse. Its charming, pumpkin-colored facade stands out against the rocky coastline, with a classic lighthouse design that has guided mariners for years. The lighthouse, perched on a small island, offers a picturesque and serene scene, adding a touch of history and maritime character to the landscape.
New England’s coastal communities come alive with festivals celebrating maritime heritage, fresh seafood and classic sailing traditions. Here are some must-see events for summer cruising:
Mystic Wooden Boat Show
Mystic, CT, June 27-29
A showcase of beautifully restored wooden boats and craftsmanship.
Wickford Art Festival
Wickford Village, RI, July 12–13
Renowned as one of the region’s top art festivals, it features over 200 artists showcasing diverse artwork, complemented by live music and food vendors.
Blessing of the Fleet
Narragansett, RI, July 24-26
A time-honored tradition featuring a boat parade, live music and plenty of fresh seafood.
Charlestown Seafood Festival
Charlestown, RI, August 1-3
A celebration of New England’s best seafood, plus fireworks and live entertainment.
Market Square Day
Portsmouth, NH, June 14
This festival features over 200 exhibitors, including artisans, food vendors and entertainers. A 10K road race is also part of the festivities, making it a lively day for the whole community.
Gloucester Schooner Festival
Gloucester, MA, August 27-August 31
A stunning gathering of schooners racing off Cape Ann.
Portsmouth Maritime Folk Festival
Portsmouth, NH, September 27-28
Celebrates traditional maritime music with performances by folk artists from around the world.
Salem Haunted Happenings
Salem, MA, October 1-31
A fun excuse to dock in Salem for a month-long festival of ghost tours, maritime legends and Halloween events.
Windjammer Days Festival
Boothbay Harbor, ME, June 22-28
A week-long event featuring parades of historic windjammers, fireworks and dockside celebrations.
Maine Lobster Festival
Rockland, ME, July 30 - Aug 3
The ultimate celebration of Maine’s favorite crustacean, complete with boat tours and maritime contests.
Eggemoggin Reach Regatta
Brooklin, ME, August 2
The ERR is the largest wooden boat regatta in the world and takes place between Deer Isle and Brooklin.
Eastport Pirate Festival
Eastport, ME, September 4-7
A lighthearted festival with pirate reenactments, a boat parade and plenty of dockside fun.
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