Nantucket Christmas Stroll

We had heard so much about it and always wanted to go. Shops decorated with festive lights and kept open late into the evening, carolers dressed in their Victorian finest singing and parading the streets, restaurants serving their most delicious specialties, and shopping. Lots of shopping. Finally, we did it!

It’s hard not to get into the spirit at the Nantucket Christmas Stroll. There is excitement in the air from the minute you round the Brant Point Lighthouse with its iconic green wreath and single red bow.

It has been a tradition in Nantucket since 1973. The first weekend in December is dedicated to welcoming visitors from near and far. It didn’t start out that way though. The Nantucket Stroll originated nearly 50 years ago as a way to entice locals to stay on the island to shop instead of traveling to the mainland of Cape Cod. A number of merchants decided to keep their stores open into the evening, entertaining shoppers with cocoa, tea, wine, and holiday goodies while they bought holiday gifts. 

As the years passed, more and more folks attended, new events were added, and its popularity increased exponentially.

It is easy to understand why it has become so popular. Nantucket is charming during the summer, but it is absolutely magical during the Christmas stroll. 

We Found Many Fun Things to Do

  1. Main Street Shopping. The stores are welcoming and beautifully decorated. As the lights go down, the lighted trees along the main cobblestoned streets are festive and fun. There’s even a contest for the best lighted tree and best decorated storefront.

  2. Festival of Trees at the Whaling Museum. Hundreds of community-crafted trees are on display for you to marvel over.

  3. Santa’s Village Marketplace. Held in the Stop & Shop parking lot, there are over 40 booths with items to purchase for unique gift giving.

  4. Santa’s Parade. Arriving on a coast guard boat, Santa then transitions into and travels the cobblestone streets on a vintage fire truck. When the parade is over, there is a meet and greet with Santa. Plenty of picture opportunities with the kiddos.

  5. Walking Tours. There are narrated tours of the historic downtown, ghost walks identifying haunted homes, and walks past whaling-era mansions and the 1746 windmill.

  6. Brant Point Lighthouse. It is a very short walk from the downtown area and a great place to take selfies and to watch the boats go by. 

  7. Waterfront Christmas Lights. While the main storefronts in the downtown area are festively lit and decorated, you’ll also find wonderful homes along the waterfront equally impressive. Meander to see the famous row boat anchored not too far from shore with a fully-decorated and lighted Christmas tree.

  8. Entertainment. From skating with Santa to watching theater workshop mini performances and ugly sweater contests, there are plenty of activities to keep you entertained. 

  9. Book Signings and Author Meet and Greets. At Mitchell’s Book Corner and Nantucket Bookworks, you’ll have a chance to meet many different authors who will be available for book signings throughout the weekend.

  10. Advent Worship Celebration. The First Congregational Church offers a special worship celebration with the lighting of candles to mark the beginning of the season.

  11. Concerts. An outdoor stage near the 20-foot Christmas tree in the middle of the downtown area is where you’ll find bell ringers and local musicians performing.

  12. Nantucket Lighthouse School’s Yuletide Fair. Unique handcrafted items, heirloom-quality gifts, baked goods, and holiday craft activities await.

  13. People Watching. From groups of ladies fully dressed as trees, adults in Grinch costumes, and more people than not wearing lighted reindeer antlers, there’s entertainment in watching visitors. We met “Papa Elf and Buddy” who caused quite a stir!

  14. Nantucket Christmas Carol Production. Held biennially, this is A Christmas Carol story, nantucket-style with Scrooge being part of the whale oil trade. 

  15. Restaurants Galore. Nantucket boasts some of the best restaurants. You’ll want to sample the culinary delights offered by the island’s talented chefs.

Where to Stay

It’s important to note that some hotels require either a two-night or a three-night minimum, and reservations should be made well in advance. There are folks who make the stroll an annual event so their hotel reservations are made for the next year while they are attending in the current year. 

We stayed at the Jared Coffin House, which is a very short walk from the Wharf. Beautifully decorated, this landmark mansion was built in 1845 by a seafaring captain, Jared Coffin. 

Many people stay at the White Elephant, which opens in December just for the Christmas stroll. It is a short walk to the Brant Point Lighthouse as well as downtown and is quite luxurious.

The Union Street Inn was named by Boston Magazine as the best boutique hotel in Nantucket. It is in the heart of the action.

The Bayside Resort offers a special Stroll Package with a two-night minimum that includes a round-trip ferry ticket, breakfast each morning, and a late checkout on Sunday.

There are many other places to stay. I recommend visiting the Chamber of Commerce.

Pro Tips

  • If you don’t have the time or desire to stay on the island for the entire weekend, attending the stroll for just one day is still enjoyable. Arrive early and stay until the last ferry leaves. That way you can still see the twinkling lights.

  • You don’t need a car. Everything is within walking distance.

  • When you arrive on the island, visit the Nantucket Chamber of Commerce at Zero Main Street, second floor, for a copy of the Official Stroll Program. Consider purchasing their Nantucket stroll collectible pin.

  • Wear good walking shoes. Heels make it hard to navigate the cobblestone streets. 

  • Buy a Nantucket stroll scarf at the Boat Basin store. Each year offers a different design.

  • Visit the Brant Point Lighthouse for a great Christmas card photo. Since the stroll is the first weekend in December, you’ll have plenty of time to get cards made.

  • Book dinner reservations in advance. 

Held the weekend after Thanksgiving, the Nantucket Christmas Stroll is the perfect thing to do to set a festive mood for the Christmas season.

I would imagine that 2024 will be quite an extravaganza with the 50th anniversary coming up. If you’re considering going, it might be wise to plan now. 

If you’ve been to the Nantucket Stroll, what are some of your favorite things to do? Do you have ideas on other fun holiday events to attend? Let us know in the comments.

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