The ultimate list of twenty activities for Nantucket Christmas Stroll 2021!


1. 47th Annual Christmas Stroll
December 3-5
Downtown Nantucket
Stroll. Is. BACK! The crown jewel of the Nantucket offseason makes its official return to the social calendar this weekend. Wear comfortable shoes and festive clothing to hit the town to shop for holiday gifts in many of the island’s boutiques. For more information including main stage entertainment details, when to see the Town Crier ring in Stroll, the store-front decorating contest, Santa’s arrival time to Town, and more, click here.


2. Nantucket Book Partners Book Signings
December 3 + 4 All Day
Mitchell’s Book Corner and Nantucket Bookworks
It’s a festival of authors this Stroll Weekend! Stop by either Mitchell’s or Bookworks all weekend and you never know who you’ll run into – Elin Hilderbrand, Nat Philbrick, and Nancy Thayer are just a few of the names on the schedule. Copies of books will be available to purchase on site. For more information and the complete list of signings and authors, click here.


3. Rafael Osona Auction
Preview December 3 from 10:00 am – 5:00 pm, Auction Dec. 4 at 9:30 am
American Legion Hall, 21 Washington St. 
Stroll on down to pick up a holiday trinket or two at Rafael Osona’s auction of the season. Known for their wide assortment of classic antiques, unique treasures, and vintage finds, you’re sure to scoop up a one-of-a-kind holiday gift for anyone special on your list. For more information, click here.


4. Epernay Wine and Cocktail Tastings
December 3 + 4 from 3:00 – 5:00 pm
Epernay Wine & Spirits
Make some mistletoe magic this weekend with this pair of beverage tastings! Friday afternoon the focus will be on cocktails, and the team at Epernay will be whipping up Mistletoe Mules and Goodwill Gin Fizzes for some good (responsible) fun. Saturday afternoon will be wine time, featuring some of their top selections of the season. Cheers! For more information, click here.


5. Beach Rides Book Signing
December 3 from 4:00 – 6:00 pm
Centre Pointe
New coffee-table staple Beach Rides by John Annetti and Whitney Hubbell of Johnny Vacay will be centre stage at Centre Pointe this Friday afternoon. The authors will be in-store to sign copies amidst all the impeccable home treasures of Centre Pointe. For more information, click here.


6. Stroll Soiree and Book Signing at Susan Lister Locke Gallery
December 3 from 5:00 – 7:00 pm
Susan Lister Locke Gallery, 28 Easy Street
Revel in the finer things in life this weekend with a little jewelry and literature to pair. Renowned designer and decorator Molly Skok will be on hand to sign copies of her book Mally’s Little Handbook. For more information, click here.


7. Dreamland’s Deck Series
December 3 from 7:00 – 10:00 pm
The Dreamland
Stroll, rattle, and roll up to the Dreamland deck for a dance party like no other this weekend. Series producer DJ Pete Ahern will be spinning the tunes along with star DJ Braun Dapper. Best Dressed will win 4 tickets to the next Decks event over Daffodil Weekend! For tickets and more information, click here.


8. TWN’s Forever Plaid: Plaid Tidings
December 3 + 4 at 7:00 pm
Bennett Hall
Offering up the best of Forever Plaid, Forever Plaid: Plaid Tidings is filled with Christmas standards that have all been “Plaid-erized.” Enjoy classic music sung in perfect harmony and delightful tunes all ages will love. For tickets and more information, click here.


9. White Heron’s A Christmas Carol
December 3 + 4 at 7:30 pm
White Heron Theatre
Nantucket’s newest favorite holiday tradition is back, and so are the spirits visiting Ebenezer Scrooge! Take the whole family to enjoy this cherished tale with an island twist and revel in the true spirit of Christmas. For tickets and more information, click here.


10. Dalton & The Sheriffs Christmas Stroll Party at the Box
December 3 + 4 at 10:00 pm
The Chicken Box
Jingle all the way to the Box for everyone’s favorite visiting Boston band as they tear down the house for the holidays. Expect a mix of classic country, seasonal sing-alongs and plenty of merriment. Don’t forget your vaccine card or a negative COVID test. For tickets and more information, click here.


11. St. Mary’s Christmas Fair
December 4 from 9:00 am to 2:00 pm
St. Mary’s Parish Center
You’re going to need some fuel for all that strolling, and the St. Mary’s Christmas Fair has you covered. Enjoy sausages, hot dogs, hamburgers, clam chowder, chili, vegetarian chili, donuts, coffee and more as you peruse holiday basket raffles and decor in the Parish Center. For more information, click here.


12. NLS Yuletide Fair
December 4, 10:00 am – 2:00 pm
White Elephant Ballroom
This can’t-miss (and free!) community event is truly one for the kids. Featuring unique handcrafted items, heirloom quality gifts, a holiday bake shop, craft activities and more, the Fair is your one-stop shop for all your holiday needs and supports the Lighthouse School. For sponsorship details and more information, click here.


13. Shop Santa’s Village Nantucket
December 4 from 10:00 am to 3:00 pm
Foot of Main Street
Shop dozens of island brands, small companies, and local vendors in this favorite Nantucket holiday market tradition. Make sure to bring along charged phones for Venmo, credit cards, and cash so you are prepared for all payment types! For more information, click here.


14. Wreath Making Workshops
December 4 + 5, Various Times
Bartlett’s Farm
Decorate your own custom wreath to add an extra special Nantucket touch to your home this holiday season. Embellishments will be on-hand, including scallop shells, pine cones, berries, glitter sprays, fancy baubles, and more. The Bartlett’s Farm staff will be available to answer questions and give design advice. For tickets and more information, click here.


15. Wine Tasting and Trunk Show
December 3 – 5
Shop til you drop and the bubbles won’t stop at currentVintage this weekend. Enjoy the marvelous finds of the “Decades Sustainable Chic” trunk show from vintage luminary Cameron Silver of the iconic boutique Decades in LA, featuring eco luxury gifts. Holiday wine and bubbles will be served alongside in style. For more information, click here.


16. Kit Noble Gallery Pop-Up
December 3 – 5
Samuel Owen Gallery
Take a piece of the island home with you when you go with an incredible piece of art from fine art photographer and N Magazine Chief Photographer Kit Noble. For more information on Kit’s work at Samuel Owen, click here. For more information on Kit’s photography, click here.


17. ReMAin Nantucket’s Envision Resilience Nantucket Challenge
December 3 – 5
2nd Floor of Thomas Macy Warehouse, 12 Straight Wharf
If you have not yet had the chance, check out the exhibition from ReMain’s ERNC and learn  more about how we as a community can prepare for the effects of climate change. The showcase features student design proposals from five participating universities to show how Nantucket businesses and residents can live with sea level rise. For more information, click here.


18. Faraway & Sister Ship Canned Goods Drive
December 3 – 5
Sister Ship at Faraway Hotel 
In the season of giving, Faraway is making it easier than ever to give a little extra to those who need it most. Support the Nantucket Food Bank by bringing in your canned good donations to Sister Ship at any time during Stroll, and you’ll receive a complimentary hot apple cider in return. For more information, click here.



19. Cookie Decorating
December 3 – 5
Easy Street Cantina
Calling all strolling kids! This 19-year tradition is still going strong and is better than ever. Kids of all ages can pick up cookie-decorating kits from Easy Street Cantina including freshly baked sugar cookies, colored sprinkles, candies, and fresh frosting. Made in partnership with the Nantucket Cookie Company. For more information, click here.


20. NHA’s Festival of Trees
December 3-31
The Whaling Museum
’Tis the season to deck the halls, and no one decks them better than the local decorators in the Festival of Trees! This annual NHA events kicks off Stroll weekend and benefits Nantucket’s leading historical association all month long. For tickets and more information, click here.


More from Nantucket Magazine

N TOP TEN: September 16 – 22, 2016

The ultimate activities guide for September 16 – 22, 2016. 1. Wine...
Read More