Winter Weekend on Nantucket

Just because it’s not summer doesn’t mean you don’t have plenty of reasons to plan a winter weekend on Nantucket! The winter season is a quiet, beautiful time to stroll the empty beaches, unplug and curl up with a book, and (perhaps best of all) grab a bed, meal, and souvenir at bargain off-season prices.

At the invitation of the Nantucket Hotel and Resort, I was lucky enough to spend a winter weekend on Nantucket back in January, 2013.

I set out from Keene, New Hampshire, on a Friday morning, and after crossing over the Bourne bridge into the Cape (no traffic in winter!), I made a beeline for Pain D’Avignon. Tucked down a side street next to the airport, it’s a marvelous bistro/cafe/bakery, and the ideal “last stop” before heading on to the outer Cape, Martha’s Vineyard, or Nantucket. I grabbed a coffee, baguette, and some biscotti. After stocking up it was time to park and board the ferry, which was busier than I thought for a cold winter weekend. Despite the arctic wind on the deck, I had to venture out to snap a few photos of the chairs draped in ice. Looks cozy, doesn’t it? Brr.

Upon arriving in Nantucket, I was met at the dock by Jamie Holmes, General Manager of the hotel. In truth the hotel was so close to downtown I could have walked, but since it was a cold day and I had a suitcase, the ride was much appreciated!

Along the way, Jamie told me about the hotel’s history. It was originally opened as “The Point Breeze” in 1891, a grand hotel boasting amenities such as running water, gaslights, croquet lawns, and a ballroom — all with stunning sea views. It had weathered several highs and lows during its long history, including new owners, name changes, and periods of closure, but its most recent transformation came about in 2012, when Gwenn and Mark Snider bought the property and put it through a major restoration and renovation.

Parked in front was the old-fashioned green and yellow bus the hotel uses in-season to transport guests to and from the ferries.

Inside, the sunny lobby was awash in nautical blues and whites…

…along with a nod to the island’s whaling past in a prominent spot behind the reception desk. The steampunk-style (sort of Victorian meets industrial) mechanical whale from local outfitter ModVic is certainly worth seeing!

The scheme in the lobby continued into my guest room, which was large and comfortable with plenty of options for seating, sleeping, and planing your Nantucket winter weekend.

Only it turns out I didn’t have to plan much, because Jamie had already arranged for me to grab a bite in the onsite Breeze Bar & Cafe with local fisherman Charlie Sayle and his son. Because it was scallop season (please see the bay scallop flatbread pizza below), we’d hoped to be able to head out onto the water to do some real scalloping, but because the temperature was so low it wasn’t possible.

After an informative meal (where I learned that 99% of Sayle’s bay scallops head off-island to points all over the country, and that The SeaGrille Restaurant was where I should go for the best seafood dinner on Nantucket) Jamie offered to take me on a guided driving tour of the island. Because it was too cold for biking and I hadn’t brought my car, I was grateful for the invitation. Nantucket isn’t enormous, but it’s still too big to see entirely on foot.

The first stop on our driving tour was Bartlett’s Farm, Nantucket’s oldest and largest family-owned farm.

Open year-round, the farm’s on-site market offers seasonal fruits and vegetables (plus a wide selection of organic foods, prepared meals, and household staples) as well as a garden center. Above the market is a space used for the popular lectures and events that take place throughout the year. The topics range from food and nature to sustainable energy.

Cisco Brewers is another year-round Nantucket institution. The brewery/distillery/winery delights drinkers region-wide, and for those on-island, no stay (or perhaps weekend) is complete without a visit for a drink, tasting, or to enjoy the frequent live music.

After leaving the bar we headed out for a look at Cisco Beach. It had snowed just enough the night before that the road looked more like a white carpet than a thoroughfare.

Then it was time for a look at the island’s famous 1745 windmill before the all-important stop at Downyflake Doughnuts, a top family restaurant/doughnut draw for both locals and visitors since the 1940’s.

Next it was time to check out Sankaty Lighthouse, which looked picture-perfect thanks to the fresh snow.

For a dose of island charm, we drove through the village of Siasconset (or ‘Sconset), with its tightly clustered cottages (wee little things compared to the ship captain houses downtown and large mansions scattered elsewhere on the island), many which used to be fishing shacks. It was a bit too cold for the beautiful ‘Sconset Bluff Walk this time, but I put it on my list for my next warm-weather visit.

And then, circling back towards town we made a stop at Charlie Sayle’s retail and takeout spot — Sayle’s Seafood. Here, Angela gave us a peek at the day’s scallops, along with a look at a waving (unfortunate) 5 1/2 pound lobster.

After wishing the lobster godspeed, we headed for Brant Point Lighthouse, which was established all the way back in 1746…

…and then made a quick stop at Steps Beach, which is accessed by a narrow path between two private houses, so the path is marked (like many others) with a “Public Way” marker to let you know you’re not trespassing. Even in winter, the view is stunning.

Finally, we stopped to admire the Jethro Coffin House, known as the “Oldest House” because it is the sole surviving structure from the island’s original seventeenth-century English settlement. It was built as a wedding gift in 1686 for Jethro Coffin and Mary Gardner, and has been owned since 1923 by the Nantucket Historical Association.

In 1987 the house was struck by lightning and nearly cut in half, but was carefully restored by the NHA. Historic properties find they are in very loving and admiring hands on Nantucket, which makes the island an especially beautiful and interesting one to visit for those of us looking for more than a peek into the past.

The tour over, I thanked Jamie for his hospitality and headed to my room, but as night fell, I couldn’t resist a walk downtown. Lit up inside, the quaint and snug shops on Main Street shone from the inside out like dollhouses, their light spilling onto the cobblestone streets below.

On Sunday morning, I stopped in at the Petticoat Row Bakery [since closed], one of the many fine Nantucket bakeries, for coffee and an enormous slice of bread pudding before setting out on a walk. The bread pudding at Petticoat Row is more bread than pudding, and after tasting a sample I asked what was in it. The answer was “whatever is left over at the end of the day.” My slice was spicy and fragrant, like carrot cake mixed with cinnamon and vanilla and anise. Yum!

Despite the chilly weather, icy patches (ouch), scattered snow, and bare branches, downtown Nantucket still managed to look inviting.

Iconic images are everywhere, from whales and whitewashed churches to classic cars and Murray’s Toggery Shop, official supplier of “Nantucket Red” since 1945.

While many shops and restaurants are closed for the off-season, plenty remain open, often with bargain menus or rock-bottom sales to make way for new merchandise before the spring season starts.

The Dreamland Theater is the go-to place for movies, plays, and other entertainment. Of course, if you want to head back to your room to curl up with a good book, the island has you covered there as well. Mitchell’s Book Corner on Main Street is open-year round, along with my favorite Nantucket book shop — Nantucket Bookworks.

With creaky floors, bright colors, and colorful scattered hooked rugs (most with whale motifs), the books, toys, gifts, and cards at Bookworks give you plenty to look at while you warm up.

If it’s open, you should (of course) also visit the superb Nantucket Whaling Museum. It wasn’t open when I visited, but it’s a fantastic museum anchored by a 46-foot sperm whale skeleton suspended over the main exhibit area.

After browsing my way through downtown, I headed for a small patch of beach to hunt for scallop shells. The harbor shore had frozen in a natural wave pattern, as if one moment the wave was lapping the shore, and the next, it was frozen in an icy crust.

Still, there were plenty of beautiful scallop shells to gather, some trapped under ice that I gently pried up with the toe of my sneaker so I could get to them. I think I gathered roughly 20 shells to take home for a future craft project. And despite the cold weather, I was not alone. The ducks had found where the water still flowed and rippled near the dock, and they swam and bobbed underwater in the sunshine. I tossed them my bread pudding crumbs before heading back to the hotel to gather up my things. My winter weekend on Nantucket was over, but I hope it’s only a matter of time before I’ll be back on ACK!

Have you ever spent a winter weekend on Nantucket?

This post was first published in 2013 and has been updated. 

SEE MORE:
Weekend on Nantucket | Affordable Island Fun in Photos
Cape Cod, Nantucket & Martha’s Vineyard Lighthouses | Photos
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Aimee Tucker

Aimee Tucker is Yankee’s senior digital editor. A lifelong New Englander and Yankee contributor since 2010, Aimee has written columns devoted to history, foliage, retro food, and architecture, and regularly shares her experiences in New England travel, home, and gardening. Her most memorable Yankee experiences to date include meeting Stephen King, singing along to a James Taylor Fourth of July concert at Tanglewood, and taking to the skies in the Hood blimp for an open-air tour of the Massachusetts coastline.

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