The Lobster Rally Rolls On

Two buddy boats set out to find the best lobster roll in New England.

Sampling lobster rolls in Newport, Rhode Island. Jeremy Cage

People handled the COVID-19 shutdowns in all kinds of creative ways. My wife, Pat, and I had hoped to buddy-sail our Pacific Seacraft 34, Taravana, through the Bahamas and Caribbean with our friends Teri and Lee, aboard the Hallberg-Rassy 37 Glendora, but instead, we all decided to explore the Northeast. We christened our trip the Lobster Roll Rally, and set out to taste and rate as many lobster rolls as possible throughout New England. 

We set sail up the Intracoastal Waterway in mid-March, just enough ahead of the crowd to enjoy beautiful, empty anchorages, along with space in restaurants. We explored the Chesapeake Bay in May, overindulging in crab cakes. (We unofficially christened this leg of the journey the Crab Cake Crawl.) While it was unseasonably cold and wet for much of the month, we were blessed with good wind and some cracking sailing. At night, we would alternate drinks and dinner aboard each other’s boats, increasing the fun factor and reducing the cooking workload. After dinner, we’d play cards or strum our guitars. 

We sailed into Manhattan in June and, after a two-year absence, pulled back into our home port of Rowayton, Connecticut. Friends David and Cindy, aboard their motor vessel Moondance, joined us there, and the Lobster Roll Rally began in earnest. T-shirts, lobster paraphernalia, stickers and lobster-roll rating sheets were all handed out, along with generous gin and tonics. 

After a couple of weeks of preparation, we all set out eastbound in Long Island Sound, stopping first at Northport Harbor, New York, and its beautiful Victorian-era town center. From there, we sailed northeast to Stonington, Connecticut, which first prospered in the 1790s when it was home to a large fleet of seal-hunting ships. Moondance has a shallow draft, so we all climbed aboard for a day trip to Watch Hill, Rhode Island, and an expansive stretch of pristine beach.

A rainy, cold July Fourth in Boston. Jeremy Cage

Following some spirited sailing up the coast, we moored in Jamestown, Rhode Island’s Dutch Harbor. It’s a quiet spot across from the bustle of Newport, where we sampled the Newport Lobster Shack—a solid waypoint for any lobster-­roll aficionado. Our float plan then took us to New Bedford, Massachusetts, once the whaling capital of the United States and the setting for the 1851 novel Moby-Dick. The New Bedford Whaling Museum is a must-see. It not only brings to life what the whaling trade was like, but also reveals why the town is so progressive and diverse today. Lobster rolls at the Quahog Republic Whaler’s Tavern had a new twist—a nicely toasted brioche bun—so they rated well. 

Boston Harbor was our anchorage for July Fourth. I’m English, so I felt that it was imperative to celebrate our arrival with a nice, hot cup of tea. It turned out that we needed a lot of it because the weather was dreadful. Despite the cold and rain, we had a blast. After seeking out the requisite lobster rolls, we toured the town, ate Italian in Little Italy, tried Chinese in Chinatown, and sampled pints of Guinness in the many Irish pubs. Another highlight was the USS Constitution sailing its turnaround cruise right across our bows.

Continuing north, we ventured up to the coastal fishing village of Gloucester, Massachusetts, and then through the skinny Blynman Canal up to Kittery, Maine. While we were anchored in Back Cove, Maine, some friends who live locally took us to their favorite lobster shack: the Rye Harbor Lobster Pound. Those lobster rolls won the summer for us. The lobster was fresh, plentiful, served nice and hot, and lightly basted in sherry butter for a rich, slightly sweet flavor. The pièce de résistance was an open-ended cardboard sleeve that prevents messy bun collapse. (Yes, this is something we measured.)

Rye Harbor Lobster Pound
Rye Harbor Lobster Pound: home of the winning lobster roll. Jeremy Cage

From Kittery, it was up to Portland, Maine, and the remote, rock-lined anchorages of Casco Bay. We’d made it 1,300 miles all the way up from Georgia.

En route back south, we explored the vibrant town of Provincetown, Massachusetts. During a crazy night celebrating Pat’s birthday, we got matching henna (you guessed it) lobster tattoos inked on our ankles. Lee also debuted the official Lobster Roll Rally sea shanty: “Yo ho rally my friends, along New England’s shore; yo ho rally my friends, lobster rolls for evermore.”  

LRR 2021 sticker
The official LRR 2021 sticker is now all over New England. Jeremy Cage

From P-Town, we sailed to the ­ever-buzzing Cuttyhunk, Massachusetts, and the fun raw-bar boat where they shuck fresh oysters boatside. After stops at Martha’s Vineyard and Nantucket, Block Island appeared on the horizon. There we were able to relax on the beach and drink too many mudslides in the Oar restaurant. 

Then, forces beyond our control (again) drove us to change our plans. Hurricane Henri was barreling north, so we skipped our final stops and shot home before the storm. 

At the end of August, after months of fun and many miles under our keels, the Lobster Roll Rally came to a close. Or did it? We all hope that it might never end.

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