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Winter Weekend on Nantucket

Winter Weekend on Nantucket
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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 newly reopened Nantucket Hotel and Resort, I was lucky enough to spend a winter weekend on Nantucket back in late January.

I set out from Keene, NH on a Friday morning, and after crossing over the Bourne bridge into the Cape (no traffic this time of year!), 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. Yum…

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 122-year 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 Steampuffin 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 relaxing. The latter for me included taking a hot bath, digging into my Pain D’Avignon goodies (with the help of items found in the kitchenette), and curling up on the sunny window-seat/daybed (not pictured, but off to the left) the next morning to plan my day.

It turns out I didn’t have to plan much, because Jamie had already arranged for me to have breakfast in the onsite Breeze Cafe with local fisherman Charlie Sayle and his son. Because it was scallop season, 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 breakfast (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) 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 to 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 large room for the popular lectures and events that take place throughout the year. The topics range from food and nature to sustainable energy, but on the day of my visit, Tom Berry and Liz O’Connell (executive chef and executive pastry chef respectively) from the Great Harbor Yacht Club were doing a demonstration

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. You might also want a nip of Notch whisky, the highest rated American-made single malt according to the 2012 Whisky Bible.

Be sure to say hello to native islander Pat Wynn if he’s working!

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.

After Jamie and I enjoyed our doughnut each, it was time to check out Sankaty Lighthouse, which looked picture-perfect thanks to the fresh snow.

As we continued to drive along east, Jamie pointed out a large, grey-shingled, gabled, oceanfront home that looked different from the rest, meaning it wasn’t meticulously maintained. In fact, it looked abandoned, like a Nantucket version of a haunted house. I’d love to know more about who owns it and why it’s not lived in…

Up next 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.

And then, circling back towards town we made a stop at Charlie Sayle’s retail and takeout spot — Sayle’s Seafood.

Here, the lovely 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 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 Reds” 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 Starlight Theatre and Cafe offers both cozy meals and movies, making it the perfect winter night out.

The newly opened Dreamland Theater is another option 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 you can see what I thought in another Nantucket post — Budget Weekend on Nantucket.

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, which reminded me of childhood stories where a character touches another and he turns to stone. It was 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. Scallop shell success!

And despite the cold weather, I was (of course) not alone on the beach…

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!

Looks like the ducks hope so, too.

Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

Aimee Seavey


Aimee Seavey


As Yankee's Digital Editor, Aimee manages, produces, and promotes content for Yankee's digital and social media initiatives. A lifelong New Englander, she loves history and a good Massachusetts South Shore bar pizza.
Updated Friday, March 1st, 2013

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7 Responses to Winter Weekend on Nantucket

  1. beth masterman March 1, 2013 at 10:58 pm #

    What a wonderfully written article- photos and all! The Nantucket Hotel and the Island’s charm are so perfectly portrayed here. This piece brought me back to the time I spent at The Nantucket during Thanksgiving 2012 with my family. Gwenn and Mark Snider have resurrected a hotel for the ages, blending the charm of the Island’s New England past with all the amenities a contemporary traveler expects and enjoys. This one is a ‘must’ for families large and small.

  2. Ingolf Schruff March 2, 2013 at 7:28 am #

    A great article about a wonderful island and hotel. Too bad that it is so far from Europe……

  3. Lori Pedrick March 2, 2013 at 2:50 pm #

    Great blog Aimee! So many awesome pictures. Great overviews and details and I’m loving the grids. Glad you had a nice and inspiring trip. Thanks for sharing your experience. Now I’m itching to go!

  4. Courtney April 22, 2013 at 9:01 pm #

    I will add a winter trip to my bucket list!

  5. Laurie Watts June 16, 2013 at 11:11 am #

    What a fantastic trip ! I love New England and what a perfect way to perk up a dull winter. Not sure what the winters are like on Nantucket. When did you take this trip?

    • Aimee Seavey June 17, 2013 at 10:35 am #

      Hi Laurie! My winter weekend visit took place in January. While some of the shops and restaurants are closed during the off season, plenty are still open to make a trip worthwhile.

  6. Cathy Leffler February 8, 2014 at 9:50 am #

    Hi Laurie,
    In July 2012 we walked the bluff in Sconset and actually saw someone sitting on the porch at the “abandoned looking” house. The windows were open and it definitely looked like someone was staying there. Looks like the house has alot of history and an incredible view.

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