Nantucket Stroll | An Insiders Guide

New England has it’s share of scenic and spirited holiday festivals; but there is nothing quite like The Nantucket Christmas Stroll, the annual festival held the first weekend of December on the tiny island 30 miles out. A celebration of the season, as well as as the last shopping and dining hurrah for most businesses for the winter, it has become a tradition we always have on our calendar.

From the moment you round the harbor and spy Brant Point Light all dressed up in her holiday wreath, the chill on the top deck of the ferry quickly turns to warmth as you slow down and pull into the dock.  Are those sleigh bells ringing in the distance…

It’s no secret that Nantucket is one of our favorite New England destinations, and summer with her warm days and long nights are certainly a beautiful time to enjoy the island. But it is the off season events we love the best.  We usually kick off Spring with the Daffodil Festival in April and heading to Stroll in December is the perfect bookend to the year.  As with any event, it can be overwhelming for first timers to find their way and make the most of their trip.  Here is a list of some things you won’t want to miss. And remember, there is never a wrong way to enjoy Nantucket! You will find your own favorites and memories to start an annual tradition.

Main Street is all aglow and lined with community decorated Christmas trees and twinkling white lights that sparkle all along the cobblestone streets.  The merchant windows are all decorated beautifully and the sidewalks are buzzing with revelers, all dressed up in fun and festive holiday styles. Stroll draws people from all over the country to enjoy the charm of the island and celebrate the spirit of the season. The feeling of coastal holiday cheer truly abounds.



getting there

The start of your day will vary a little depending on your own timing, but we would highly recommend the fast ferry on Seastreak out of New Bedford. Check the times and availability as it is usually limited this time of year and be sure to book a round trip ticket in advance. It is also always recommended that you get there at least an hour before departure to ensure a good seat.

There are other high speed ferry options out of Hyannis including The Steamship Authority or the Hy-Line Cruises.  All things being equal, the one you choose will depend on the time you want to leave as they both have different schedules.  Both offer day parking for an additional fee.

Once on board you have your choice of seating inside the boat or outside on the upper decks.  All boats offer a bar and a cafe style menu of snacks and small bites.

deck the halls...

You will have spotted on of our favorite holiday decorations when you were still on the ferry. We love how Brant Point Lighthouse is always the symbol of any season and for Stroll she is always decked out with a large wreath and red bow. Make your way out to see her for some great holiday photos.  As you head back into town, the Christmas tree in the little red sunken row boat off Old North Wharf and Easy Street is probably the most iconic of all the island holiday sites. Walk slowly past the stores to take in the beautiful window boxes and festive displays, with some like Lemon Press featuring window painting by local artists such as Meredith Hanson.  Standing tall and bright at the top of Main Street is the town tree, with the smaller community trees lining up and down the sidewalks and cobblestone streets. And no trip into town should go by without a stop into Flowers on Chestnut – the store is a vision of decorations, flowers and lights.

oh christmas tree...

The Nantucket Whaling Museum is always a dramatic and memorable visit, but during the holiday season, it is absolutely magical. Each year, the Nantucket Historical Association transforms the museum into a gorgeous gallery of Christmas trees decorated by local businesses, residents, schools, non-profits, artists and community groups. The sky’s the limit for creativity and themes on over 75 trees. The price of general admission includes the decorations as well as a tour of the museum, which offers a rich history of Nantucket’s whaling industry. While we usually say you can be in and out of the museum in one hour or less, during Stroll it’s worth taking extra time  to walk through and enjoy all the decorations and displays.  There is something for everyone to enjoy and you’ll find it hard to pick a favorite!

here comes santa claus...

On the Saturday of Stroll weekend, Santa Claus officially comes to town around 12:30 pm. A good spot to watch his arrival into the harbor aboard a Coast Guard cutter boat is by the gazebo and shops along Straight Wharf. He then walks down the wharf, and then parades to the Jared Coffin House downtown to meet with children.

The weekend is also filled with tons of activities for all ages that are organized by The Chamber of Commerce.  Do them all, do one or do none, it’s up to you! Stroll calendar guides are available all over town or you can visit the official website for all the latest information.

photo credit: Saltaire Nantucket


tie one on...

As you walk around town, you will notice that almost everyone is sporting variations of an official woolen scarf. Don’t be left out in the cold!  Every year there is a new version that is sold in local retailers like Town Pool or Nantucket Boat Basin Shop; but they sell out quickly so if you want to grab one, this should be one of the first shopping stops. 

come sale away...

Unlike the island, the shopping in Nantucket is far from quaint! You’ll find well known brands like Ralph Lauren, Vineyard Vines and Lilly Pulitzer. I prefer local favorites like Nantucket Looms, 28CentrePointe, DAWN, ACK 4170, Piping Prints, Current Vintage and Stephanie’s. No shopping trip to Nantucket is complete without a stop at Murray’s Toggery Shop, famous for the original Nantucket Red apparel brand.  I also can never get enough of Monelle, Blue Beetle, Gracie Geier and Milly Grace. As we mentioned earlier, this is the last hurrah for the local shops before closing for the winter and to make way for new inventory in the spring, you’ll find amazing deals in all of the stores.  This is a great time to stock up on summer staples or make the splurge and grab that cashmere sweater you’ve been after.



eat, drink and always be merry

It doesn’t take a lot to get into the spirit during Stroll, but when it’s time to kick it up a notch, there are so many fantastic restaurants to enjoy a cup of good cheer and a warm and cozy meal.  Some of our favorite spots to soak in the atmosphere are CRU, Sister Ship, Breeze Restaurant and the view and Bloody Marys never go unnoticed at the Brant Point Grille. Reservations are definitely recommended this time of year for most places.



be our guest...

Make it a weekend with a stay at one of the local hotels. The Nantucket Hotel, is a family friendly resort + spa that is one of the few year round properties, and their holiday decorations are equally as a memorable as any around town. Another lovely spot is Hotel Pippa, a smaller boutique hotel right in the heart of downtown that is great if you’re traveling without small kids. And the recently opened Faraway Nantucket is a gorgeous modern hotel that offers dining and a central location.

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