Travel Destinations

New England Towns

Take a Journey to Discover American History and Charm

New England

During the past six years of living and cruising aboard our boat MV TAPESTRY, we explored beautiful and historically significant harbors along the eastern seaboard of the United States and Canada. We also encountered fellow boaters who hadn't yet ventured north of Chesapeake Bay. Perhaps an introduction to New England's quintessential waterside towns will tempt them to head north. Some of these New England towns date back to the 1600s; none have lost their timeless allure.


Mystic Seaport - historic towns - marinalife
Mystic Seaport | Jason Condon


Along the Connecticut River a few miles up from its mouth in Old Saybrook lies the graceful town of Essex, which was settled in 1648. The lucrative Triangle Trade (see sidebar p. 112) from the New England colonies lured men from this area to the sea and shipbuilding industry. A British attack in 1814 burnt 28 vessels at anchor or under construction, leading Essex newspapers of the time to call this raid the worst disaster to befall the new country since the War of 1812 began. Today, this New England gem is composed of three villages Essex, Ivoryton and Centerbrook which offer lovely places to explore for food, drink and entertainment.

Things to See & Do: Connecticut River Museum, The Griswold Inn (serving travelers since 1775), Essex Steam Train & Riverboat, Pratt House (17th century home museum), historic pubs such as the Black Seal, art galleries on Main Street, and classic colonial-era architecture.

Where to Dock: Saybrook Point Resort & Marina


This quaint town along the Mystic River resides in the towns of Groton and Stonington. The area was settled in the 1600s after experiencing conflict with the Pequot Indians and Massachusetts Bay Colony, who wanted to keep the riverfront land for itself. Shipbuilding was a significant endeavor, with more than 600 ships built in the late 1700s. Visitors now flock to the historic downtown area near the bascule bridge to find quaint shops, restaurants and charming New England buildings and street life.

Things to See & Do: Mystic Seaport and the whaling ship Charles W. Morgan, Mystic Aquarium, Mystic Museum of Art, and the famous movie, Mystic Pizza.

Where to Dock: Mystic River Marina


7 Seas Whale Watch - historic towns - marinalife
Chepstow Mansion in Newport, RI


On Aquidneck Island in Narragansett Bay, Newport was founded in 1639. In 1658, Jews fleeing the Inquisition in Spain and Portugal were welcomed to settle here. Newport colonists earned their living in the whaling industry and related manufacturing trades, such as sperm oil and candles. The area also garnered riches in the Triangle Trade. This coastal community comes alive in the spring with historic mansion and garden tours, events at local wineries and breweries, and strolls along the Cliff Walk to witness the picturesque shoreline.

Things to See & Do: Mansions of the Gilded Age, Touro Synagogue (oldest synagogue in America), Fort Adams State Park, Bowen's Wharf, harbor cruise to Jamestown and Rose Island Lighthouse, Naval War College Museum, International Tennis Hall of Fame, Newport Vineyards, Seal Watch Tours, beaches, red brick streets downtown, dinghy around the harbor.

Where to Dock: Bowen's Wharf



Located on Massachusetts' North Shore, Salem was settled in 1626 by a group from Gloucester seeking better land for farming. Despite a rich maritime heritage, its most famous history revolves around the Salem Witch Trials, which began in 1692 and resulted in the hanging of 19 innocent women. While 17th century stories of alleged sorcery attract visitors, the quaint town also offers a variety of good restaurants, pubs, shops, galleries and Federal-style mansions.

Things to See & Do: Salem Heritage Trail, Salem Witch Museum. Salem Witch House, Old Burying Point Cemetery and Witch Trials Memorial, Salem Maritime National Historic Site, historic buildings, wharves, replica ships, beaches, walking trails, Harbor Sweets factory tours, and Punto Urban Art Museum.

Where to Dock: Pickering Wharf Marina

7 Seas Whale Watch - new england towns - marinalife
7 Seas Whale Watch in Gloucester, MA | Massachusetts Office Of Travel & Tourism


About 40 miles north of Boston on Cape Ann, Gloucester was founded in 1623 (before Boston and Salem) and is one of the first English settlements in what became the Massachusetts Bay Colony. Early Gloucester residents subsisted on logging, farming and later fishing. A thriving granite industry also existed for a time. A visit here would not be complete without sampling the region's fresh seafood, enjoying a day at the beach, strolling around art studios and galleries, and exploring quaint buildings.

Things to See & Do: Whale watching at Stellwagen Bank National Marine Sanctuary, distillery and foodie tours, museums, Rocky Neck Art Colony, Ravenswood Trail, Stage Fort Park, Halibut Point State Park, Gloucester Military Heritage & War Memorial Trail, Soldiers of Gloucestershire Museum at Gloucester's historic docks, Fisherman's Memorial, Good Harbor Beach, Maritime Gloucester and Hammond Castle Museum.

Where to Dock: Cape Ann's Marina Resort



Portsmouth lays at the mouth of the Piscataqua River, which forms the border between Massachusetts and New Hampshire. American Indians inhabited the coastal area for thousands of years before Europeans arrived in 1630. Incorporated in 1653, its principle businesses included lumber, fishing and shipbuilding. Portsmouth participated in the Triangle Trade, and slaves were integral to its prosperity. The Industrial Revolution created opportunities for wealth from relationships with the mills located up river. Known as a foodie haven, Portsmouth hosts eateries for grab and go meals to take along on biking or hiking trails and other outdoor attractions. The art and music scenes are exceptional, as are places to shop, golf, swim and enjoy family-friendly activities.

Things to See & Do: Strawberry Banke Museum, unique small businesses, sales tax-free shopping, Portsmouth Brewery, gardens at Prescott Park and its arts festival for live concerts, movie nights, and outdoor musicals, Portsmouth Harbor Lighthouse, boat tour to Star Island on the Isles of Shoals.

Where to Dock: Marina at Harbour Place


Stonington, CT - new england towns - marinalife
Stonington, CT | Wikimedia Common

Stonington & Deer Isle

Stonington is on the southern part of Deer Isle on Penobscot Bay in the Mount Desert area of Maine's coast. Its first inhabitants were the Abenaki Indians, dating as far back as 6,100 years ago. The town was settled by Europeans and incorporated in 1897. Stonington was named for its quarries that produced granite for important U.S. structures including J.F.K. Memorial, Yankee Stadium, Boston Museum of Fine Arts and The Smithsonian. Lobstering contributed to its booming economy, and the town's seafaring reputation grew by providing full crews for America's Cup Races in 1895 and 1899. Other major attractions: local lobsters, a nice selection of restaurants and pubs, and artists' galleries, studios and shops that often stem from Haystack Mountain School of Crafts.

Things to See & Do: Deer Isle Lighthouse Trail, Deerinature self-guided nature trails, Deer Isle Village walking tour, harbor tours, Waterfront and Fox Island Thoroughfare, Lobster Boat Races in the Thoroughfare, Crockett Cove Woods Preserve and Barred Island Preserve hiking trails.

Where to Dock: Billings Diesel & Marine


Belfast is situated in Maine's upper Penobscot Bay. Once a territory of the Penobscot Tribe, Belfast was first settled in 1770 by Scots-Irish proprietors from Londonderry, NH. The town has experienced hardships and rebounds throughout its history. Mostly abandoned during the American Revolution, it was rebuilt as a shipbuilding center. Wealthy maritime barons erected Federal, Greek Revival and Italian style mansions around town. The advent of refrigeration in 1900 shifted the economy to harvesting seafood for Boston and New York markets. Shoe manufacturing and the poultry industry employed many until the 1970s. Credit card giant MBNA established a call center in the 1990s, and shipbuilding was reestablished on the waterfront. Outdoor and indoor music venues, galleries, boutiques, fresh lobsters, and hiking trails overlooking the sea are just a few reasons to visit this town.

Things to See & Do: Belfast Harbor Walk, Belfast City Park, Passy Rail Trail, Belfast Historical Society & Museum, Cuckold Lighthouse, Belfast Farmers Market, Main Street, Celtic Festival in July, and Young's Lobster Pound.

Where to Dock: Front Street Shipyard

Monhegan Island

Monhegan Island is about 12 nautical miles off the mainland in Maine's mid-coast region. The island's colorful past includes a 1614 visit from Captain John Smith and pirate ships in 1717. A trading post was established to conduct business with the Indians selling cod and furs. Fishing still dominates the island's economy, and since the 1890s artists established a colony with active studios and galleries around town. Shops, restaurants and gorgeous scenery complete this bucolic getaway.

Things to See & Do: 17 miles of rustic trails in the rocky headlands with spectacular views, the Lighthouse, the Ice Pond, Monhegan Museum of Art & History, local artist galleries, beaches, The Meadow (gathering place and public water supply) and Tercentenary Tablet commemorating John Smith's visit.

Where to Dock: Monhegan Island Harbor

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