As the holiday season approaches, Nantucket comes alive with festive spirit and cherished traditions. From artful wreath displays to the highly anticipated Christmas Stroll, there’s something for everyone to enjoy. Here’s a look at some of the events happening on the island from November through December, making this the perfect time to soak in the beauty and charm of Nantucket while in the “off-season”.

November Events

The Nantucket Historical Association’s Festival of Wreaths kicks off the holiday season with a celebration of creativity and community spirit! Join us for the Preview Party—a festive evening of light bites, drinks, and an exclusive first look at this year’s community-crafted wreaths! This event features an incredible variety of wreaths, crafted by islanders, local businesses, schools, and organizations. From traditional greenery to unique designs, the Festival of Wreaths captures the heart of Nantucket’s holiday spirit. It’s a perfect chance to shop for one-of-a-kind holiday gifts and support local artists! Click here for tickets and more information.

Are you brave enough to take the plunge on the 28th?! The Cold Turkey Plunge is a fun-filled event where participants dive into the chilly waters of Nantucket Harbor, all in the name of charity. This event benefits the Weezie Library for Children and is a great way to start Thanksgiving day with some laughs and community spirit. Register and learn more about the fun here!

Kick off the holiday season on the 29th on Main Street with the Chamber of Commerce’s Annual Tree Lighting. Join friends and family as the island’s main square transforms into a winter wonderland with sparkling lights and festive, holiday cheer. It’s a magical evening filled with carols, hot cocoa, and the warmth of our community. Learn more.

December

As December rolls in, we look forward to one of the most magical weekends of the year: the Christmas Stroll. Now celebrating its 50th year, this iconic event transforms Nantucket with holiday charm, from Santa’s arrival on his nautical sleigh to the festive sounds of carolers in Victorian attire, there’s something for everyone! The holiday magic continues with craft shows, a European-style Christmas Marketplace, and family-friendly activities that make it an unforgettable experience. Click here for all the details on times, parking, and everything you need for a fun, festive visit!

During the entire month of December, the NHA’s Festival of Trees will also be on display, featuring an array of stunning trees designed by local artists, merchants, and organizations. This event showcases the creativity and talent within our community, making it a must-see for anyone looking to embrace the holiday spirit. Lee Real Estate’s tree is back again this year—be sure to come check it out! Learn More.

Finally, get ready for holiday fun, and don’t miss the Red Ticket Drawing on December 24th, a chance to win exciting prizes while supporting local businesses. The Nantucket Island Chamber of Commerce continues its tradition of promoting local businesses during the holiday season, encouraging everyone to shop local and be part of the island’s vibrant community.  Lucky winners will be drawn from tickets collected all month long, adding an extra dash of excitement to your Christmas Eve celebrations. Remember, you’ve got to be present to win, so come join the festivities! Learn how to get in on the action here!

Looking for a Last-Minute Place to Stay?

If you’re planning to visit Nantucket during the holiday season, we have some fantastic property opportunities that are available. Check out two of our favorites below:

134D Main Street:

This rental property is still available for you and your family to stay in and enjoy all the festivities Nantucket has to offer this season! This is a beautiful, newly renovated two-bedroom, two-bathroom on a quiet shell street just steps from all the holiday action on historic Main Street! This charming rental offers the best of both worlds with historic character and all the modern comforts, making it ideal for a cozy, merry getaway.

With an open, sunlit living and dining area, a well-equipped kitchen, and an inviting living room, this home welcomes you to relax and enjoy the colder season in style- perfect for unwinding after a day at the Festival of Wreaths or Christmas Stroll. A convenient mudroom to off-load your coats, and plenty of room for the whole family, make this rental the ideal place to make memories on Nantucket this holiday season.

20 Hussey Street

Escape to Nantucket for a long weekend this fall or stay for Thanksgiving and enjoy spending time in this newly renovated six-bedroom, six-bathroom home in the Old Historic District. Perfect for Thanksgiving, this home gives you easy access to Nantucket’s festive lineup – from cheering on brave souls in the Cold Turkey Plunge on Thanksgiving morning to shopping for unique, local gifts at the shops downtown.

With six bedrooms, six bathrooms, and thoughtfully designed indoor and outdoor spaces, this home is perfect for gathering with enough space for your loved ones. Enjoy evenings by the fireplace, share meals at the elegant eight-person dining table, or savor the crisp autumn air on the front porch or spacious back deck. Although Christmas Stroll is fully booked, fall weekends and Thanksgiving are still available—don’t miss your chance to experience the charm of Nantucket in the off-season!

 

As we gear up for the festive season on Nantucket, be sure to mark your calendars for these exciting events that capture the magic of the holidays.  Whether you’re enjoying the festivities with the community or looking for a cozy place to stay with the family, the island has something special for everyone this season. Contact Lee Real Estate today to find the perfect Nantucket getaway this upcoming season, don’t wait – book now!