Nantucket Christmas Stroll Guide

The Nantucket Current has gathered many of the scheduled Christmas Stroll activities and put them in one place for our readers. If there is an event you'd like included in this guide, please email David Creed at davidcreed@n-magazine.com.

Whaling Museum's Festival Of Trees All Weekend

Every year community members, local merchants, nonprofit organizations, artists, artisans, and schoolchildren design magnificent trees displayed in the Whaling Museum for visitors to enjoy throughout the season.

Beginning on Friday, December 1 the Whaling Museum's Festival of Trees will be open to the public every day from 10 A.M. - 4 P.M. (with the exception of Christmas Day. Islanders and members get free admission.

Proceeds benefit the Nantucket Historical Association's year-round educational outreach and preservation efforts.

Artist Association of Nantucket's Stroll Pop-Up Gallery Open All Weekend

Members of the Artists Association of Nantucket (AAN) will be showing their big gallery upstairs at 12 Straight Wharf - presenting an opportunity for shoppers to shop local. This gallery will be open from 10 A.M. to 4 P.M. Also, The Holiday Small Works exhibition will be on display through December 22 at the Cecelia Joyce & Seward Johnson Gallery, 19 Washington St., in the heart of Nantucket’s Cultural District. Currently, the gallery is open Tuesday – Saturday, 10 A.M. – 5 P.M., closed 2-2:30. During Stroll weekend, the gallery will also be open Sunday, Dec. 3, 11 A.M. – 4 P.M.

St. Paul's Christmas Stroll Concert On Friday

Sustainable Nantucket's Farmers & Artisans Markets Friday & Saturday

The Dreamland's Stroll Party Featuring The Hess Twins Friday Night

Join the Nantucket Dreamland for their third annual Dreamland Stroll Party on the second floor of The Dreamland Friday, December 1st from 7-10 P.M. The well-known DJ duo - the Hess Twins - will be performing your favorite top 40, classic, and holiday hits to dance the night away to. Dress in your finest Stroll garb and the Dreamland will have a contest for the best dressed with the winner taking home four tickets to their Daffodil weekend party.

The Dreamland will have a Step-and-Repeat for photos, a mirror photobooth, along with a cash bar and some lite bites as well. The Dance Party will take place in the Studio Theater with awesome lighting and decorations. Food and areas to relax will be available in the Harborview Gallery and deck. This event sells out every year, so don’t delay in getting your tickets.

General Public: $40 (+$3 service fee)
Dreamland Members: $35 (& no service fee)

Ticketed, 18 and above; 21+ wristband
All Sales Final. No Refunds or Exchanges.

You can buy tickets by clicking here.

Pip & Anchor Dance Party On Friday

Only limited tickets remain, but you can buy yours by clicking here.

Christmas Stroll Book Signing Extravaganza At Mitchell's Book Corner, Nantucket Bookworks Friday And Saturday

Friday December 1, 2023 at Mitchell's Book Corner

3 P.M. - 5 P.M.
Christy Cashman
author of The Truth About Horses

Saturday December 2, 2023 at Mitchell's Book Corner

10 A.M. - 11 A.M.
Leslie Linsley
author of Christmas on Nantucket

11 A.M. - 12 P.M. 
Alison Barone
author of Nantucket Nelly
& the Rainbow Boat Race

12 P.M. - 1 P.M.
Betsy Tyler
author of A Thousand Leagues of Blue

1 P.M. - 2 P.M.
Nathaniel Philbrick
author of In the Heart of the Sea
and Travels with George

2 P.M. - 3 P.M. 
Nancy Thayer
author of All the Days of Summer and A Very Nantucket Christmas

3 P.M. - 4 P.M.
Jacquelyn Mitchard
author of An Inconvenient Scandal
and The Deep End of the Ocean

4:30 P.M. - 5:30 P.M.
Elin Hilderbrand
author of
The Five-Star Weekend
and the Winter Street Series

Over at Nantucket Bookworks

10:30 A.M. - 11:30 A.M. 
Hannah Reynolds
author of Eight Nights of Flirting

St. Paul's Christmas Market On Saturday

Lighthouse School's Yuletide Fair On Saturday

A holiday fair to benefit Nantucket Lighthouse School will be held in the White Elephant Ballroom at 19 North Water Street on Saturday, December 2 from 10 a.m. to 2 p.m. The Fair will feature handcrafted holiday items, heirloom quality gifts, a curated art show, craft activities for children, and more.

First Congregational Church's See a Reindeer’s View Of Nantucket Event On Saturday

On Saturday, December 2 from 10 A.M. to 12:30 P.M., climb the tower of the First Congregational Church for an amazing view of Nantucket and have your photo taken with Santa’s reindeer. Treats & goodies upon arrival. All donations will benefit The Warming Place on Nantucket.

The First Congregational Church is a short block or two from downtown Nantucket at 62 Centre Street.

Shop Santa’s Village On Saturday

On Saturday, December 2 from 10 A.M. to 3 P.M., meander through the Chamber’s Christmas Stroll Marketplace in the Stop & Shop parking lot at the foot of Main Street. Indulge in delectable food and beverages as you chat with friends and browse a variety of handcrafted gifts and merchandise sold by Chamber members and non-profit organizations.

Live Entertainment On Main Street On Saturday

On Saturday, December 2 from 10 A.M. to 4 P.M., stop by the Main Street Stroll Stage to enjoy performances by Theatre Workshop of Nantucket, The Boys & Girls Club, Susan J. Berman, NCMC Vocalist and Youth Chorus Caroling, The Accidentals & Naturals, Nantucket Ballet, and more. This is a Nantucket Chamber event. The Kazoo Marching Band will meet at the Nantucket Community Music Center (56 Centre Street) and play from 9:15-10 a.m.

Town Crier Rings In Christmas Stroll Late Saturday Morning

On Saturday, December 2 at 11:45 A.M., Nantucket’s Town Crier will ring in Christmas Stroll and lead visitors to Straight Wharf to greet Santa Claus. This is a Nantucket Chamber of Commerce event.

Santa Claus Comes To Town On Saturday

On Saturday, December 2 at 12 P.M., watch Santa arrive via a Coast Guard Cutter and join the parade as it travels up Main Street & across Centre Street to the NHA Whaling Museum. This is a Nantucket Chamber event.

Santa Meet & Greet On Saturday

On Saturday, December 2 from 1-2 P.M., meet and take photos with Santa at the Nantucket Whaling Museum. Don't forget to bring letters to the North Pole to drop in Santa’s mailbox. This is a Nantucket Chamber event.

Stroll Celebration, Photos With Santa At Susan Lister Locke Gallery On Saturday

On Saturday, December 2 from 2-4 P.M., celebrate Stroll weekend with the Susan Lister Locke Gallery. Santa will be in the gallery from 2-4 P.M. for photo ops and wish lists. Enjoy special flash sales when the bell rings. Also featuring the wonderful artwork of Anne Marie Bratton. The gallery is located at 28 Easy Street on the waterfront. There will also be a 15% off Holiday Sale through the weekend.

Ugly Sweater Contest On Saturday

On Saturday, December 2 at 2:30 P.M., join the Nantucket Chamber of Commerce at the top of Main Street for an ugly sweater contest with honorary judge - Santa Claus. You know you have one, so why not get a prize for wearing it? Get ready to strut your stuff at 3 P.M. This is a Nantucket Chamber of Commerce event.

Community Caroling On Main Street Saturday Evening

On Saturday, December 2 from 4:30 - 6 P.M., join the island’s Victorian Carolers for a sing-along on the steps of the Pacific National Bank on Main Street to close out another amazing Christmas Stroll. This is a Nantucket Chamber of Commerce event.

First Of Advent Worship Celebration On Sunday

On Sunday, December 3 at 10 A.M., enjoy beautiful music, candlelight, and a warm welcome at this worship as we enter Advent Season. Sunday School for children; coffee and treats following the service. This will take place at the First Congregational Church, which is located at 62 Centre Street.

Sugar Plum Social At Lemon Press On Sunday

Join the Lemon Press (41 Main Street) on Sunday, December 3 from 2:30-4:30 P.M. for an enchanting afternoon filled with delightful treats, music, and merriment. Enjoy a delicious menu of finger sandwiches, pastries, and tea curated by Lemon Press, and mingle with some of your favorite characters from the Nantucket Nutcracker! Photo Ops, Raffle, Silent Auction, a special Nutcracker Preview, and more. Entry is $20.

Jolly Jam Skate At Nantucket Ice On Sunday

On Sunday, December 3 from 3-6 P.M., head to the Nantucket Ice Rink for live music, dance performances, food, cookie & cocoa bar, activities for kids, and more. Santa will make an appearance to join the kids on the ice. This event presented by Nantucket Ice and the Nantucket Chamber of Commerce. The Nantucket Ice Community Rink is located at 10 Backus Lane. Admission is $25 for adults, $10 for age 14 and younger – skate rentals included.