How to Spend the Holidays on Nantucket in 2025
- nantucketislandmar
- 16 minutes ago
- 3 min read
Photo via Nantucket Chamber
The holidays on Nantucket are pure magic. Picture cobblestone streets lined with twinkling lights, historic homes dressed in evergreen wreaths, and the salty air turning crisp as you stroll between local shops and cozy restaurants. While summer often gets the spotlight, the fall and winter holidays offer a completely different kind of beauty – a slower pace filled with community spirit, island traditions, and a warmth that feels uniquely Nantucket.
Here’s how to experience the best of the island this holiday season.
Can't-Miss Holiday Events
Tree Lighting Ceremony: November 28
The day after Thanksgiving marks one of Nantucket’s most beloved traditions. At 4 PM, the Annual Tree Lighting and Community Caroling begins, transforming Main Street into a sea of twinkling lights and music. More than 150 trees come to life as locals and visitors sing along to holiday carols together.
Main Street will be closed from noon to 6 PM, and the best way to enter the ceremony is from Main Street itself. Caroling lyrics are available on the Nantucket Chamber of Commerce website, and QR codes will be placed throughout the area for easy access. It’s an evening filled with joy, tradition, and true community spirit, making it an unforgettable start to the season.
Nantucket Stroll Weekend: December 4-7
One of the island’s most iconic celebrations, Stroll Weekend turns downtown into a winter wonderland. Shop windows glow with holiday décor, carolers fill the air with music, and Santa makes his grand entrance down Main Street. Local artisans and shops offer one-of-a-kind gifts, perfect for checking off your holiday list.
If you’re planning to attend, book accommodations early because hotels and rentals fill up quickly for this beloved weekend.
Festival of Wreaths: November 24-29 and
Festival of Trees at the Whaling Museum: December 5-31
Kick off the season with the Festival of Wreaths from November 24–29, then return in December for the Festival of Trees, which runs from December 5–31. Each event features stunning creations designed by local artists, businesses, and nonprofits, displayed throughout the Whaling Museum. Whether you go with friends, family, or for a quiet afternoon to yourself, this is one of the most enchanting holiday experiences on the island.
Where to Eat, Sip, and Celebrate
Warm up after your holiday adventures at some of the island’s favorite spots.
A lively setting for cocktails or dinner, perfect for gathering with friends after the Tree Lighting.
A cozy, welcoming restaurant with a robust menu and delicious sushi that everyone will love.
Ideal for a relaxed breakfast or coffee before a day of exploring.
Many local restaurants offer special menus for the holidays or New Year’s Eve, so reservations are recommended if you’re visiting in December.
Shop Local: Gifts You Can Only Find on Nantucket
Holiday shopping on Nantucket is part of the magic. Skip the big-box stores and explore the island’s locally owned boutiques and artisans instead.
Timeless clothing and gifts.
Beautifully curated reads.
Handcrafted blankets and home goods that make perfect gifts for the colder months.
Each store has its own charm, and every purchase supports the island’s small business community.
Cozy Winter Activities Beyond Downtown
For quiet moments away from the festivities, take a walk along Steps Beach or Brant Point to enjoy the peaceful winter scenery. Stop by Cisco Brewers for live music and a local drink, or visit Bartlett’s Farm for fresh produce and holiday treats. Even in winter, the island’s natural beauty shines.
Thinking of Making Nantucket a Part of Your Holidays Every Year?
Whether you’re visiting for a weekend or dreaming of spending every holiday season here, there’s never been a better time to make Nantucket your home away from home. From historic cottages to ocean-view retreats, I’d love to help you find a place where your own island traditions can begin.
Reach out today to explore available listings or start planning your perfect Nantucket getaway.
