Nantucket Christmas Stroll (Here We Stroll Again)

A few years ago, in want of some place unique to visit for an anniversary getaway, I did an internet search for “best places in America at Christmas,” and Nantucket’s annual Christmas Stroll weekend topped the list of results. Stroll, as it is called for short, started as a way to encourage people to shop locally and as a last tourism push for the end of season before the the shops, hotels, and restaurants largely close for the winter. Fifty-one years later, the event has officially become known world-wide!

We had a phenomenal time in 2021 at our first Stroll, so I was thrilled we were able to go back for a second time to enjoy this absolutely magical event. Nantucket is already a sight to behold, with all the grey shingles and cobble-stoned streets. Add in wreaths, window boxes brimming with seasonal trimming, garland on fences and gates, and adornments as far as the eye can see—it’s my idea of holiday heaven. Let me take you through our three-day weekend of Stroll revelry, one bit of cheer at a time.

We stayed at the Nantucket Hotel and Resort, which was Stroll central! Their antique red firetruck drives Santa in the Christmas parade and also gives plenty of rides to guests over the course of the weekend as well.

We made a return visit to the Tap Room at the Jared Coffin House Thursday evening for dinner, the same place we ate in 2021 when we visited. The picture on the left is from our first dinner there and the right is this year.

The unofficial Stroll slogan is “Sip. Shop. Stroll. Repeat.” And as you’ll see, we did just that. One of our first stops downtown on Friday was Murray’s Toggery Shop, which is the home of the original “Nantucket Reds,” those red pants meant to fade over time. The selection is so fun to see.

We were on our way to the Whaling Museum for their annual Festival of Trees (there were 88 decorated Christmas trees on display this year), and we had to stop to take a picture outside the Dreamland Theater with the statue of Mr. Rogers. Fred Rogers was a regular summer resident of Nantucket and has been named an honorary patron saint of the island. The theater presents an annual Fred Rogers Good Neighbor Award to a selfless community member.

Speaking of Christmas trees, there are about 175 live trees lining the the Main Street and downtown, decorated by local businesses, groups, and individuals. This martini-themed tree with glasses and olives was done by a local Italian restaurant.

And this lighthouse tree was decorated by the Harbor Master. Fantastic!

Not to be outdone, how about this adorable car parked downtown, all decked out for Stroll weekend?

All that sightseeing will work up an appetite, so we stopped for lunch at The Club Car. The restaurant is in a restored 19th century train car, so it was a cozy place to sit down and have a cup of amazingly good New England clam chowder. At night, it's a piano bar (and a lively good time).

Christmas Stroll weekend is the time to break out your most festive attire (you’ll see plenty more in my upcoming Stroll day pictures—this is just a warm-up.) Is this picture giving off high voltage, or is it just us? Also, no, I don’t know these women. You make friends very easily on Stroll weekend!

I had to snap a picture of this Christmas-clad beauty in the hotel lobby.

She was there while we were, listening to the Victorian carolers. The carolers also stroll the downtown throughout the weekend, too.

Our dinner Friday was at The Seagrille and, among other things, we enjoyed these caviar tater tots. I do not exaggerate when I say they are a near-life-changing experience. If you hate New England, detest Christmas, and are afraid to travel…go there for these. It will be worth it.

And now, the big day. We were relieved the weather was better than forecasted and we woke up to a sunny day. As they say in Nantucket, Happy Stroll!

The people watching alone is a sport. Each one gets better…

But this inflatable reindeer was hilarious and was Clint’s favorite of the day.

Before long, you can feel the streets start to get crowded. Everyone starts to gather to wait for this guy: the town crier. He rings his bell to announce it is time to walk down to the wharf to watch Santa come in on the Coast Guard boat, where he will board the firetruck and begin the parade through town!

And sure enough, down at Straight Wharf, it’s the man of the hour, coming in off the boat.

No sooner had Santa walked by than we ran into this guy dressed as baby Jesus, “Just keeping the Christ in Christmas,” he proclaimed. Then his entourage showed up (and sadly, I could not manage a picture of them all—an entire manger scene complete with wise men, angels, shepherds, a camel, and even a man with a light-up star overhead on a fishing pole! 10/10.

You know what? It was all so spectacular, even this one was feeling the Christmas spirit.

What to do after all that excitement? Lobster rolls, of course! Warm, with butter, cole slaw, and pickled vegetables.

What an incredible bonus that one of my favorite Nantucket authors, Elin Hilderbrand, was also in town for a book signing Saturday. I was ecstatic to meet her and have her sign a copy of *Winter Street,* her novel about a family and their chaotic holiday season on Nantucket.

I’m not going to lie, we ate lobster every chance we got. And then we took turns thanking the heavens we are not allergic to shellfish.

I once heard a comedian joke, “If you love lobster and you hate your wallet, Nantucket is a great place for you.” It’s true, it is an expensive place to visit any time of year. It is also a charming place every day of the year, but especially during the holiday season. Is it worth risking the weather, and paying to have the Christmas Stroll experience? As a two-timer now, emphatically, YES! I am already thinking the third time will really be the charm, as they say (and plotting and planning even better, more over-the-top outfits). We came, we saw, we strolled. And with any luck, there is a repeat in our future. Happy stroll!

Nantucket Christmas Stroll (Here We Stroll Again)

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