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Photos by Dori Arrington

Portsmouth, New Hampshire

It’s got the sophistication of Boston, the food and vibe of Portland, the charm of Kennebunkport and the history of Plymouth all rolled into one.


Imagine a New England town with the sophistication of Boston, the food and vibe of Portland, the charm of Kennebunkport and the history of Plymouth all rolled into one. Welcome to the seaport city of Portsmouth, New Hampshire, one of New England’s most overlooked gems.

As a boater, I can understand missing Portsmouth on a run from Cape Cod to Portland—at only 18.5 miles long, New Hampshire has the smallest shoreline of any coastal state. In a fast Down East cruiser, you could miss it in the time it takes to eat your lobster roll at the helm, but passing it by would be a big mistake. While New Hampshire may technically have the smallest coastline, if you add all the inland water you can access by boat, that figure jumps to over 200 miles.

When cruising northbound, once you’ve cleared the twin tower lights of Thacher Island, Massachusetts, 26 nm on a heading of 002° magnetic will lead you straight into the Piscataqua River and Portsmouth Harbor. The river splits into two sections around New Castle Island. The north channel serves as the boundary between New Hampshire and Maine. Downtown Portsmouth sits on a bluff along the southern shore, and Kittery, Maine, lies along the northern shore. On the Maine side, the Piscataqua is divided again by Seavey Island, home of the Portsmouth Naval Shipyard. Once visited by George Washington and Thomas Jefferson, it is the nation’s oldest shipyard and an important element of the country’s maritime past and present. There are numerous marinas along both shorelines, but caution is warranted, as the tidal flow is significant with a swift current.

On the south channel of the river, you will find Wentworth by the Sea Marina, Hotel and Spa, a historic upscale property perched high above the river overlooking protected coves, perfect for paddle boarding or kayaking. The marina is run by Safe Harbor, and is the perfect place to base yourself for a visit to the area. The grand Wentworth by the Sea hotel dates to 1874 and is a premium property operated by Marriott. When the hotel was built, it was the largest wooden structure on the New Hampshire coast. In its restored splendor, it is no less impressive today.

The village and Island of New Castle are easily toured by bicycle, with the historic village-center a short ride from Wentworth. On your ride, stop at Great Island Park for an easterly view across the Piscataqua. Centered in your view from the park is Wood Island, with its 114-year-old lifesaving station and picturesque Wood Island Light. For years the station served as home to the brave “surfmen” who were part of the U.S. Life Saving Service, the precursor to our modern Coast Guard. As your ride continues, you will pass the current Coast Guard Station along with the ruins of Walbach Tower, a fortification built by the townspeople in just one night to protect their homes and Portsmouth’s Harbor from the British.

Once you’ve ridden this far, in just two more miles across two more islands, you’ll find yourself in historic downtown Portsmouth. Rides like this make the folding bikes we keep in the Lazarette of Liberdade two of our most treasured possessions. ­After days at the helm, a bike ride into town is good for the mind and body.

Upon arriving into downtown Portsmouth, stop to get your bearings and some refreshment at the Tuscan Market. Located at the base of Congress Street, across from the Old North Church, the Market is the perfect starting point for exploring downtown.


Portsmouth is not just a time-capsule of the area’s past, or a New England tourist’s bubble—it is a lesson in how a city blends its rich history into a vibrant part of modern life. All of this is overlayed onto an active industrial port city. A good example of Portland’s ethos is Strawbery Banke Museum, a restored neighborhood made up of 39 historic buildings in the heart of downtown. In a setup reminiscent of Colonial Williamsburg, the buildings are open to tour, with many staffed by actors in period-dress to help you understand the area’s important contribution to the city’s founding and the industrialization of a young nation.

If Portsmouth and New Castle are not enough to keep you entertained on your visit, you can always walk to Maine. That’s right—just across the Memorial Bridge is Kittery, Maine. Kittery was the first town incorporated in Maine and an important fishing village then and now. Ferries from Kittery also visit nearby Isle of Shoals, a group of small islands about six miles offshore of Portsmouth Harbor.

New Hampshire may have the smallest coastline, but it has an oversized collection of fascinating places to visit, many of which are found in the greater Portsmouth area.

This article originally appeared in the November 2022 issue of Power & Motoryacht magazine.