Seas~ons Greetings: A Nantucket Christmas Stroll

Nantucket is located southeast of mainland Massachusetts. Tiny and quaint, this island has a ton to offer. Historically a whaling community, Nantucket has grown into one of the most well established tourist destinations, both nationally and internationally. 
We first visited Nantucket seven years ago on our honeymoon and it didn’t take long for us to fall in love with all of its enchanting offerings. 
With dreamy nautical views, cobblestone streets, five-star lodging and world-class dining, Nantucket has something to offer for everyone. 
Many choose to visit during the warmer summer months, but this post is a testimony to the festive charm that decorates the island during that beloved first weekend in December.

Nantucket Christmas Stroll

Legend states that in 1973 a few loyal islanders in Nantucket, Massachusetts wanted to help the island economy by preventing locals from taking their Christmas business to the surrounding mainlands. That year on the first Friday in December, businesses kept their stores open an extra few hours so that locals could do their holiday shopping right there on the island. Known as the first stroll, that Friday decision proved to be a festive success. Shoppers were treated with seasonal food and beverages as they perused gifts and holiday accessories. Now, 47 Christmas Strolls later, this traditional event is still held the first weekend in December and has become nationally and internationally recognized as the ultimate Christmas experience. Complete with caroling, shopping, Christmas tree decorating and lighting, as well as a parade, festive beverages and of course the arrival of Santa, this annual event is a must-experience and a beloved local tradition for the quaint Island community. ​

When To Stroll

The annual Nantucket Christmas Stroll takes place the first weekend in December. Midday, during that Saturday, the Town Crier officially rings in the Nantucket Christmas Stroll prior to heading down to the wharf where Santa is greeted from his arrival on a Coast Guard cutter. 
While the main happenings take place that first weekend, the festivities actually begin the day after Thanksgiving when hundreds of decorated Christmas Trees lining the main streets of the town are illuminated, including the large "talking tree" located at the top of Main Street. 

How To Get There

Ferry  - The most popular way to get to Nantucket is by ferry from Hyannis, MA which offers options for High-Speed ($40 one way and 1 hour) and Traditional Ferry ($18.50 one way and 2 hours) which can be mixed and matched to fit your schedule. Complete ferry schedules and information can be found here. Keep in mind that for Stroll weekend the High-Speed ferry reservations are booked months in advance.
*If you are looking to travel to Nantucket during the summer season there are also ferry options from New York City and New Bedford, MA.
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Air - Nantucket Memorial Airport is a public airport on the south side of the island that offers flights from many US destinations which can be booked from here.

How To Get Around 

Stroll - The town of Nantucket is very walkable especially on Stroll Weekend so take advantage of the streets being closed and see all that this town has to offer by foot.
​*Remember to bring good walking shoes! 
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Public Transit - Nantucket does offer a public bus transit for anyone looking to take a few moments away from the main street festivities. 

Where to Lodge

Staying within walking distance to Main Street is certainly recommended for convenience since most of the happenings take place there. Lodging can book up fast for this weekend so we advise making arrangements pretty far in advance to ensure your best stay. 

​RECOMMENDED Lodging

76 Main: *We might be somewhat biased since this is where we stayed on our honeymoon when we visited Nantucket. It's the only boutique hotel located on Main Street, offers a wonderful brunch with incredible comfort throughout each room in the house. It's no wonder that it was named a Conde' Nast Traveler Readers' Choice Award in 2019. 
​Greydon House
The Cottages at the Boat Basin
Jared Coffin House
Nantucket Inn
Harborview Nantucket
White Elephant Nantucket: * Five Star Hotel & Nationally Recognized 

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Airbnb is always an option, especially if you want to choose a location outside of the immediate downtown, perhaps closer to Jetties beach or Sconset. Once again, we highly advise booking these in advance since lodging tends to book quickly and prices increase as stroll weekend approaches. 

Wine and Dine

Throughout Stroll weekend many restaurants will offer specials and dining experiences tailored for the stroll festivities. These can be found in the annual stroll brochure but it's also a good idea to research any favorite restaurants prior to your visit. We highly recommend having a dining plan prior since restaurants will be full throughout the day with lengthy wait times during peak dining times. 

​Recommended Dining

Brant Point Grill: Located within the White Elephant Hotel, the Brant Point Grill is known to offer a stroll dinner.  
Annye's Whole Foods: Stocked with organic and fresh cuisine, Annye's usually offers a few wine and cheese tastings throughout stroll weekend. 
The Gaslight: Also the prime location for live music on the island. 
Epernay Wine & Spirits: Sommelier owned and operated. With exquisite selections, this is a wonderful stop for stroll tastings. 
The Beet: Offers daily Stroll dining fun. Check out the brochure for more specifics. 
The Downyflake Doughnuts: While their doughnuts may be a staple, this breakfast spot has a ton of other traditional favorites to choose from. All of which are delicious. 
B-ACK Yard BBQ: Delicious meats and comfort food favorites. 
Corner Table Cafe: A beautiful modern dining experience that offers something for everyone. 
Oran Mor: A lovely, upscale dining experience with a cozy atmosphere. Perfect for a special holiday dine. 
Keepers: Casual Comfort Food with a laid back vibe. 

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What To Do

Rock Around The Christmas Tree

The sight and scent of those annual traditional spruce's begin making their debut in Nantucket the day after Thanksgiving when hundreds of seven foot trees are set up to line the streets of downtown. Each tree is decorated by a local business or organization with their own personal touch. Don't forget to stop by the chamber to cast your vote for the best tree and storefront. 

Additionally, at the top of main street a 20-foot 'talking tree' is displayed. That's right, don't forget to stroll right by the beaut and you will get an earful.  This emblem of Stroll weekend is decorated by a chosen local artist each year and lit the weekend after Thanksgiving. 

Annually, the Jared Coffin House Garden's host a remembrance tree where you can write a loved ones name on a scalloped shell ornament to be displayed on the tree. 

And... incase you still need more Christmas Trees to enchant your Stroll weekend be sure to check out the Festival of Trees at the Nantucket Whaling Museum. This is a month long event featuring over 80 trees creatively and uniquely decorated by locals to create a transformed museum wonderland. 

Shop til' you drop

Stroll weekend began as a way for locals to stay on the island to shop for their Christmas gifts and while this hasn't changed, it has broadened to a larger audience. Now, not only do Nantucket residents shop locally, but stroll weekend brings in visitors from all over to support the island while exploring unique and affluent merchandise. From boutiques and stores recognized world-wide, to local shopping options, there's truly something for everyone and it's worth just stopping in and seeing what great sales and gift options are available. 

Contest, Decorations & Fun! 

The weekend fun is filled with multiple contest from tree decorating to costumes and sweaters. Be sure to check out the Stroll brochure for specifics about where, when and how to get involved in the competive fun. 

Exercise with A Guided Walk

That's right! There's no better time to get some exercise than during a holiday stroll. In addition to your own Christmas strolling down main street, why not sign up to participate in a walking tour where you can learn more about the island? Past stroll weekends have offered a variety of walking options to choose from including:  
- Mansions of the Cliff & Brant Lighthouse Walk 
- Nantucket Walkabout 
- Wilderness Walk through Stump Swamp and Norwood Farm
- Ghosts of the Island walks
- Historic Homes Walk 
​- Hummock Pond Walk

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Attend a workshop

Throughout the weekend there are a handful of offered workshops where you can learn a new trade. These range from wreath making to calligraphy and are featured in the Stroll Brochure so be sure to keep an eye out for the opportunity to pick up a new skill. 

Go to a show

The island theatrics are one you won't be disappointed in. Over the weekend a variety of concerts and theatre presentations will take place. The Theatre Workshop of Nantucket and the White Heron Theatre usually both offer beloved seasonal favorites and throughout the weekend restaurants and stages that are set up downtown will offer a variety of musical entertainment. If you decide you would like to participate there is also an opportunity to join carolers as they stroll while singing some of Holiday favorites. 

Enjoy the local literary Scene

The Island has housed and currently does host many literary talents that you can not only learn about, but can even meet and support through your purchases.
Head over to Mitchells Book Corner during your stroll to check out great literature and even some local authors who would love to greet you during the weekend. I particularly loved meeting bestselling authors Nancy Thayer and Elin Hilderbrand and having them autograph a few copies of their Christmas novels which made great seasonal reads as well as Christmas gifts for others.
Other prestigious authors such as Steinbeck and Melville have connections and were inspired by the quaint island which you can learn more about when you book your spot on a guided literary stroll. 

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Craft Shows

The entire weekend offers a range of craft shows that house local artistic talent. These events are publicized in the Stroll Brochure and are a must-see. There's a ton of great, hand-crafted, unique finds that can make that perfect Christmas gift for friends and loved ones. 

Santa Claus is coming to town

Both children and adults alike cherish the annual tradition of greeting Santa as he arrives at the wharf via boat. After his nautical arrival, Santa then makes his way up Main Street, sometimes even riding on a vintage fire truck. The streets are lined with excited viewers as Santa makes his way through the streets and throughout the weekend there are a number of opportunities to meet, greet and have your photo taken with Santa. 

extra Tips & Tricks

* Our last Stroll we decided to wake up before the sun and take the ferry from Hyannis, arriving on the Island just in time to enjoy a breakfast as Downyflake. We took the last ferry back to the Cape that evening. This fit our schedule perfectly for that weekend, but we do think that staying on the island would be a more relaxed option.
* Book your ferry reservation in advance. 
​* Plan your dining in advance. Lines and wait times for reservations can become very lengthy.
* This is a festive weekend so wear your holiday gear. 
* Wear layers and comfortable shoes. There can be a brisk coastal air while outside walking around but, most stores and restaurants will offer a cozy atmosphere to warm up in. Keep in mind that there are many cobblestone streets downtown so you will want to leave those heels in the closet this time. 
* Bring a large day bag/purse for storing all of those purchases as you're walking around. 
* Taxi prices increase during this weekend so we recommend walking or taking the bus if you choose not to bring your own car. 

Happy Strolling!

Share The Journey

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Photo Credits

*All photos used in this post are the sole content of BestCaptured*