Skip to main content

Local knowledge: Portsmouth, New Hampshire

More than a century ago a local writer referred to Portsmouth, New Hampshire, as “The Old Town by the Sea.” Its connections to the nautical past still run deep.

Portsmouth is home to the world’s only sailing gundalow — a shallow-draft barge that was common in the Gulf of Maine’s rivers and estuaries.

Boaters will find no other place like it in the Northeast — an eminently walkable destination of great restaurants, waterfront bars, theater, concerts in the park and historic buildings, all crowned by a busy working waterfront. Check it out, and you’ll realize that the tidal pulse of the Piscataqua River is still the heartbeat of this town.

Inbound skippers may find themselves sharing the channel with a 38,000-ton tanker and tugs, or occasionally with a nuclear submarine. No problem. The channel is wide and well-marked. As you proceed upstream from the sea toward the three architecturally stunning bridges crossing the river from New Hampshire to Maine, you’ll pass lighthouses, abandoned forts and Colonial-era homes on a gracious shoreline. You might encounter a commercial dragger or long-liner operating from the fish pier on Peirce Island. You’ll certainly see the military-grade RIBs patrolling the perimeter of the Portsmouth Naval Shipyard. Piloting your own boat up the Piscataqua puts you smack into a heady fleet of pleasure craft, workboats, elegant yachts and the world’s only sailing gundalow.

It’s stimulating and enchanting, but there is a hitch. Portsmouth boasts one of the fastest tidal currents in America. No local skipper takes it lightly, but that awesome current is manageable. Try to avoid the maximum flood or ebb, at least on your first visit, and you will find those cross-grained waters more welcoming.

The approach is easy, with few outlying dangers. The rocky Isles of Shoals stand guard seven miles offshore, outlying sentinels for the town. Leave to starboard both red whistle 2KR, marking Kitts Rock, and Whaleback Light, an ancient granite lighthouse. From there you can pick up the first of several harbor ranges. Fort Constitution will be to port, site of one of the first actions of the American Revolution. Tours are offered.

The largest anchorage in the Piscataqua River is Pepperrell Cove, the first stop to starboard on the Maine side of the river. The Kittery harbormaster might help you find a mooring, or you can anchor on the edge of the mooring field, under Fort McClary’s distinctive hexagonal blockhouse, built in 1844. Kittery boasts a substantial dinghy dock, with a fine seafood restaurant at the top of the ramp, but its chief attraction is the splendid view from the anchorage.

Slightly farther upstream, also on the east side, Spruce Creek branches off the main stem of the Piscataqua. A fixed bridge prevents all but the lowest of powerboats from exploring the creek, so take a hard left shortly after the mouth of Spruce Creek (before the bridge) and head up the back channel. This is home to Kittery Point Yacht Yard, with the most protected transient rental moorings in the area. KPYY is a first-rate boatyard, with diesel, gas and outboard mechanics, in addition to carpenters and systems technicians. KPYY can haul good-size boats, and it provides bicycles for visitors.

Back on the main river, farther upstream on the New Hampshire side, the Portsmouth Yacht Club welcomes transients. PYC is a very pleasant club, with the best fuel dock on the river, and its muscular launch frees you from having to fool with your dinghy.

Steer past the abandoned Naval prison, a hulking castle on the river’s east bank, and swing to starboard around Henderson’s Point. Suddenly the town, the Navy Shipyard and the new Memorial Bridge unfold before you. Downstream of the bridge on the Portsmouth side are the municipally owned Prescott Park Docks. A berth there puts you in the heart of town.

Stroll across the park for a fine dinner at Mombo’s, part of the Strawbery Banke outdoor museum complex, or head for Cava, a romantic little tapas restaurant and wine bar in Commercial Alley. You’ll find the best locally sourced seafood at Jumpin’ Jay’s Fish Cafe, a 15-minute walk from the park, through the heart of the old town, and across the street from the Discover Portsmouth Center. Don’t miss the African Burying Ground on Chestnut Street, simultaneously moving and startling.

I live here and know you’ll find few places that match Portsmouth for its range of sights, navigational challenges and enticing mix of nature and history.

Jeff Bolster is a professor of history at the University of New Hampshire. A 2013 Bancroft Prize winner for his book The Mortal Sea, he has published several other titles on maritime history. Bolster and his wife cruise their Valiant 40 Chanticleer widely.

This article originally appeared in the April 2017 issue.


Greenport’s location, on the east end of Long Island’s North Fork, makes it a popular destination for South Fork and Connecticut shoreline cruisers.

Local knowledge: Greenport, New York

Greenport has always catered to mariners. The village, between New York City and New England on the easterly tip of Long Island’s North Fork, is casual and history-filled. It has stores and services within walking distance of the water, plus a fresh local food scene along the working and recreational harbor.


Bringing Chanticleer Home

As Hurricane Irma stormed toward Tortola with our boat in its crosshairs last year, I mustered every possible shred of hope.


You’ve Got Some Options On The Lower Connecticut River

The lower Connecticut River has been called one of the last great places on Earth. For boaters who’d like to explore the region, Old Saybrook, at the river’s mouth, and Essex, 6 miles upstream, are good  places to start.

The haunting ruins of an estate from the Roaring ’20s dominate the eastern end of Sheffield Island.

The Norwalk Islands: always inviting, always changing

I fell under the spell of the Norwalk Islands early in life. My first dinghy, first fish, first outboard, first stranding, first (and only) dismasting and first island getaway — a camp that would have made Tom Sawyer and Huck Finn green with envy — all occurred in that enticing little archipelago.


Tie up in one of the oldest towns In New England

Castine, Maine, is picturesque in a way that leaves words like “quaint” and “charming” sitting in the corner with empty dance cards. The only reason most Americans have never heard of the place is the reflexive Anglo-orientation of U.S. history.