Nantucket Christmas Stroll — For Whom the Belle Tolls

Let me begin by saying I love all things Christmas—who doesn’t?—and so, when Clint and I found ourselves celebrating our twentieth wedding anniversary this year on December 1, we knew we wanted to find something special and festive to mark the occasion. With COVID-closures still causing some uncertainty, we decided not to stray too far from home, but still…we wanted a bit of a get away. After some internet research, I could not believe we hadn’t found it before: Nantucket, Massachusetts has an annual Christmas Stroll that sounded like just the perfect thing. Oh, what fun, indeed!

With Christmas trees literally lining the cobblestone streets and twinkling lights everywhere you go, Nantucket (also known at the Gray Lady) was all dressed up in her holiday best for this one last hoorah before most of the island closes for the season. The Christmas Stroll brings in people from all over the country to enjoy the holiday cheer and charm of Nantucket, and believe me when I say that little town was full of the spirit of the season like few places I have every experienced. We had such an amazing time, I simply had to share it with all of you (and perhaps relive it again a bit myself). As they say merrily all weekend around the island, “Happy Stroll!”

We stayed at the White Elephant waterfront resort.
We arrived to find these gorgeous chocolates waiting in our room in front of our very own fireplace. I could get used to this!

Housekeeping left chocolate-covered cranberries on our pillows for us each night, too. Talk about sweet dreams.

We left the hotel and strolled through the cobblestone streets to the top of Main Street. This is the town Christmas tree.

The stores along the downtown all decorate trees of their own which line the streets. It was magical at night.

This is one of the most photographed spots in town for Stroll weekend, and is actually a horsefeeder.
It dresses up nicely for Christmas, doesn’t it?

Every year, the locals float a Christmas tree in a dory boat, bobbing all weekend in Nantucket Harbor.

There were lots of gorgeous window boxes along the shops. These were outside Lily Pulitzer.

And I also loved this one outside a shoe store.

Every storefront was decorated. The entire town looks like a real life Dickens village.

We found the first of many, many, many photo opportunities.

Inside the Whaling Museum, the Nantucket Historical Association hosts a Festival of Trees with over 70 decorated Christmas trees on display.
This one had a rock and roll theme.

The White Heron Theater was performing “A Nantucket Christmas Carol,” which we went to see Saturday night.
This is their tree, wearing Ebenezer Scrooge’s signature hat and cape.

And our favorite “tree” wasn’t a tree at all! The most creative entry was by the local newspaper, *The Inquirer and Mirror*, which used paper boxes stacked and decorated.

Believe me when I say that everywhere you looked, the decorations were divine.

This was one of dozens of gorgeous planters we saw; I just had to share.

All of the lights and trimmings had us feeling like getting tinseled up ourselves.

Now that you’ve had your fill of decorations, feast your eyes on some of the food we enjoyed.
Lobster rolls, anyone?

This was part of a delicious dinner. On the left, bay scallops and fresh raw oysters with caviar on the right.
Over the weekend, we also enjoyed halibut, clam chowder, clams casino, shrimp scampi, another round of lobster rolls, lobster benedicts at brunch on Sunday…I was afraid if we had stayed for one more day we might have developed a shellfish allergy simply from overconsumption!

How about an entire boat full of shrimp, oysters, and ceviche? (That boat was also much fuller before we got to it…ha!)

And last, but certainly not least, these gorgeous lobster Bloody Marys at Sunday brunch as well!

Let me rewind a bit to the main event and describe Stroll Saturday to you: we woke up to the whole town bustling. Seriously, the locals and tourists were equally excited about the event and everyone was dressed to the nines in their most merry attire and ready for the day. This was the 47th Stroll and I think everyone was even more jovial for this year after not having the event last year, making it even more fun and festive.

Everyone gathers on Main Street in front of the stage where there are local groups performing all day, singing and dancing. Around 11:45, the town crier makes his appearance to ring the bell and officially begin the walk as a big group to the wharf, where Santa is arriving via Coast Guard cutter boat. Santa then starts a Christmas parade back to the center of town and takes pictures with all the children, and then everyone is free to sip, shop, and stroll as they please!

There are crazy Christmas outfits, hats, and costumes and photo opportunities abound like nothing you can imagine. I saw more tartan plaid in 48-hours than I may have seen in my entire life. Stroll scarves are for sale and you have probably never seen so many people joyously all wearing the same accessory, greeting each other with grins,, and calling out “Merry Christmas!'“ and “Happy Stroll!” Outside of maybe the North Pole, I can’t imagine anywhere else having more Christmas spirit than Nantucket on Stroll weekend. Christmas carols were playing everywhere we went, and, I’m sorry Disneyland, but you may have to hand over the title of happiest place on earth…at least during Stroll weekend, anyway.

The Nantucket town crier, ringing in Christmas Stroll.

You didn’t think I’d let him get by me without a picture, did you?

Riding in with the U.S. Coast Guard, here comes the man of the hour: Santa Claus!

And we ran into Buddy and Papa elf! Smiling is our favorite!

There were even Dickens carolers strolling around all day singing.

If you enjoy people watching, Stroll has a lot of that, too.

Forget the ugly Christmas sweater, the tacky Christmas suit reigns supreme for Stroll weekend.

I love the matching hat and suspenders combination here.

But these ladies, in their sparkling tinsel tops and Santa pants, won the day for me!

We spent the afternoon shopping (Clint got an amazing pair of pants at a “toggery” fit for another Stroll trip!) and enjoying all the revelry.

As they say in Nantucket, why walk when you can stroll?

We were blessed with sunny, unseasonably warm weather (highs in the low 40s, mercifully), so after a gorgeous day of strolling, we ate dinner and then headed to the theater. As I mentioned, the White Heron Theater performed “A Nantucket Christmas Carol,” which was the classic Christmas Carol story with a bit of a Nantucket twist: think Ebenezer Scrooge working in the whaling industry. It was wonderful, but Clint’s favorite part was when we went to the coat check and he found a captain’s hat stashed away on a shelf, just waiting for him.

Who says I’m the only one in our family who loves a prop?

I can’t believe Christmas Stroll has been going strong for over forty years and we just discovered this wonderful tradition. If you have the chance to experience it, you won’t regret it. We are already making plans to go back—with more festive outfits next time, naturally. It was the perfect way to celebrate our anniversary and to kickstart our Christmas season. Very merry, indeed.