Dec 6 – Dec 8 all-day
Now in its 46th year, the Chamber-sponsored Christmas Stroll Weekend is an enchanting, magical tribute to the wonderment of bygone Christmases. Join us December 6th through December 8th. 
Dec 7 @ 9:30 am – 3:00 pm St. Paul's Church
Gifts, antiques, wreaths, decorations, silent auction, baked goods, and much more! Take a guided tour of the famed St. Paul’s Tiffany windows from 10 am to 2 pm. Chowder, chili & cornbread, quiche, hot dogs, … Continue reading "Christmas Market at St. Pauls"
Dec 7 @ 9:30 am – 5:30 pm Blue Beetle
Need a little help with your shopping?  Spend $50 and receive a FREE Nantucket Pop Socket.  In store only.
Dec 7 @ 10:00 am – 1:30 pm
Stroll through Town to admire the gaily decorated trees and storefronts. Place your vote for your favorite in our annual “People’s Choice Award.” Stop by the Chamber Information Table at Zero Main Street for information … Continue reading "“People’s Choice Award” Storefront & Tree Decorating Contest"
Dec 7 @ 10:00 am – 3:00 pm Foot of Main Street.
Meander through our wondrous Christmas Market and celebrate the enchantment of the season.  Indulge in the aromas of delectable food and beverages as you chat with friends and survey a variety of handcrafted gifts and … Continue reading "Nantucket’s Own Christmas Marketplace"
Dec 7 @ 11:00 am – 5:00 pm 2 Union Street
Visit the shops and studios at 2 Union Street (just steps off Main) for holiday cheer and to shop for beautiful handcrafted jewelry by island designer Jessica Hicks and for fine cigars and glassware at … Continue reading "Holiday Open House"
Dec 7 @ 11:00 am – 4:30 pm Main Street
Stop by the stage to enjoy eclectic performances by Theatre Workshop of Nantucket, The Boys and Girls Club, Susan J. Berman, PJ Moody, The Accidentals & Naturals, and more!
Dec 7 @ 11:45 am – 12:00 pm Main Street to Straight Wharf
Gather at the Main Street stage to help our inimitable Town Crier ring in our 46th Stroll….and follow him down to Straight Wharf to welcome Santa!
Dec 7 @ 12:00 pm – 3:00 pm The Nantucket Hotel
Join us on The Nantucket Hotel’s Front Porch from 12:00 (Noon) to 3:00 p.m. for some live entertainment while you watch the Stroll revelers go by. Warm and cozy blankets are included and a light … Continue reading "Christmas Stroll Live Entertainment on The Nantucket Hotel’s Front Porch"
Dec 7 @ 12:15 pm – 1:15 pm Straight Wharf
Santa Claus comes to Nantucket Island by boat on Christmas Stroll Saturday. Watch him arrive on Straight Wharf. His arrival is usually attended by lots of admirers, so if you want to watch, come early. … Continue reading "Santa Arrives on Nantucket"
Dec 7 @ 1:00 pm – 3:00 pm Main Street
Chat with the Talking Christmas Tree All ages are enchanted by our mysterious Talking Tree, beautifully decorated for Stroll by local designer David M. Handy of Handy & Dallaire Events.  Nestle close to its branches … Continue reading "Chat with the Talking Christmas Tree"
Dec 7 @ 1:00 pm – 3:00 pm Along Centre and Broad streets and at the Jared Coffin House
The Nantucket Chamber of Commerce hosts a lineup of delightful entertainment along Centre and Broad streets during Santa’s visit.  Be sure to check out these fabulous musical acts, including Nantucket’s own Accidentals & Naturals, and … Continue reading "Entertainment at the Jared Coffin House"
Dec 7 @ 1:00 pm – 2:45 pm Nantucket Whaling Museum
Santa Visits with Kids on Nantucket Santa Claus will meet with children in the Whaling Museum Discovery Room, 13 Broad Street. Insider Tip: Buy some hot chocolate and head for the Santa line early.  This line … Continue reading "Santa Visits with Kids on Nantucket"
Dec 7 @ 3:00 pm – 3:30 pm Main Street Stage
You know you have one, so why not get a prize for wearing it? Sign up from 10:30am to 2:30pm at the Chamber’s merchandise table at Zero Main Street. Get ready to strut your stuff … Continue reading "Ugly Sweater Contest"
Dec 7 @ 4:30 pm – 5:15 pm
Join our world- renowned Victorian Carolers for a very special sing-along on the steps of Pacific National Bank at the top of Main Street. Sponsored by the Nantucket Island Chamber of Commerce.
Dec 8 @ 11:00 am – 2:00 pm
Come have your pets (or kids!) photographed with Mrs. Claus and the Elves with professional photographer Ron Lynch of Ron Lynch Photography. It’s always a festive, fun time. Proceeds benefit Nantucket Island Safe Harbor for … Continue reading "Pet Photos with Mrs. Claus and Friends"
Dec 8 @ 7:00 pm First Congregational Church
An evening of acapella arrangements
Dec 9 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 10 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 11 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 12 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 13 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 14 @ 5:00 pm – 8:00 pm Nantucket Whaling Museum
This popular family event features holiday carols, seasonal treats and child-friendly crafts in the Whaling Museum among the Festival of Trees displays. Holiday Magic is a community event, free for all children and NHA members … Continue reading "Night of Holiday Magic"
Dec 15 @ 11:00 am – 2:00 pm The Nantucket Hotel
You better watch out…Santa Claus is coming to our Sunday Brunch at The Nantucket Hotel on December 15th! We’re offering an a la Carte holiday Brunch Menu with many Christmas specials at our Breeze Restaurant … Continue reading "Christmas Stroll Brunch with Santa"
Dec 15 @ 4:30 pm Mary P. Walker Auditorium, Nantucket High School
The famous Cape Symphony Holiday Pops comes to Nantucket for the first time with a Christmas extravaganza especially tailored for the entire island community. The Dreamland presents the entire Cape Symphony and members of the Chatham Chorale along with special … Continue reading "Holiday Pops on Nantucket- The Dreamland presents the Cape Symphony Holiday Concert"
Dec 16 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 17 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 18 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 19 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 20 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 23 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 24 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 24 @ 3:00 pm – 4:00 pm Top of Main Street
Join us for the Chamber’s Annual Red Ticket Drawing sponsored by Stop & Shop this Christmas Eve at the top of Main Street. You could be one of our lucky cash prize winners of $1000 … Continue reading "Annual Red Ticket Drawing"
Dec 24 @ 5:30 pm – 9:00 pm Nantucket Hotel
Bring the family to a memorable Christmas Eve dinner in our glass-enclosed Breeze Indoor/Outdoor Terrace at The Nantucket Hotel after the Red Ticket Drawing downtown. We’re offering a spectacular, Three-Course Prix Fixe Holiday Menu – … Continue reading "Christmas Eve Prix Fixe Dinner at Breeze with Live Music"
Dec 25 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 25 @ 5:30 pm – 9:00 pm Nantucket Hotel
Bring the family to a memorable Christmas Eve dinner in our glass-enclosed Breeze Indoor/Outdoor Terrace at The Nantucket Hotel after the Red Ticket Drawing downtown. We’re offering a spectacular, Three-Course Prix Fixe Holiday Menu – … Continue reading "Christmas Eve Prix Fixe Dinner at Breeze with Live Music"
Dec 26 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 27 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 30 @ 11:00 am – 4:00 pm
Tour three NHA historic homes decorated for the holiday season! Hadwen House at 96 Main Street, the Thomas Macy House at 99 Main Street, and Greater Light at 8 Howard Street will be included on … Continue reading "Holiday Homes"
Dec 31 2019 @ 5:00 pm – Jan 1 2020 @ 12:00 am The Nantucket Hotel
It’s Back! Join us outside The Nantucket Hotel for our complimentary New Year’s Eve “Anchor Drop.” We’ll be celebrating and counting down to 2020 by dropping an anchor off the top of the Hotel. Offered … Continue reading "New Year’s Eve Anchor Drop at The Nantucket Hotel"
Dec 31 2019 @ 6:30 pm – Jan 1 2020 @ 12:30 am The Nantucket Hotel
It’s our Eighth Annual New Year’s Eve Celebration! Join us for a fun evening, waving good-bye to 2019 and saying hello to 2020 in our Grand Ballroom on December 31st. This year’s theme is “Under … Continue reading "Gala, Under the Sea New Year’s Eve Dinner & Dance (or Dance-Only) Party at The Nantucket Hotel"