Experience the charm of a Victorian Christmas on the faraway island

Picture this: Cobblestone streets twinkling with thousands of white lights. Victorian carolers in period dress harmonizing on street corners. The scent of hot cocoa and wood smoke drifting through crisp December air. Over 160 Christmas trees lining Main Street, each uniquely decorated by local schoolchildren and businesses. This is Nantucket's Christmas Stroll—a 51-year tradition that transforms our windswept island into something straight from a Dickens novel.

What Makes Christmas Stroll So Special?

Since 1973, what began as a three-hour shopping event for locals has evolved into an internationally renowned holiday celebration. The 51st Annual Christmas Stroll (December 5-7, 2025) draws visitors from around the globe who trade big-city holiday chaos for something altogether more magical: an authentic small-town Christmas where the entire community—and you—become part of the celebration.

Unlike manufactured holiday events, Stroll emerged organically from island merchants wanting to keep holiday shopping local. That community spirit remains the heartbeat of the weekend, even as it's grown into one of New England's premier holiday destinations.

Your Three-Day Stroll Itinerary

Friday, December 5: The Enchantment Begins

The weekend kicks off quietly, perfect for getting your bearings before Saturday's festivities reach full swing.

Evening Highlights:

• 7:00-9:00 PM: "It's Beginning to SOUND A Lot Like Christmas" concert at St. Paul's Church. Sip champagne and savor desserts while local musicians perform beloved carols in this historic sanctuary.
• All Evening: Victorian carolers begin their weekend-long performances throughout downtown
• After Dark: Take your first stroll down Main Street to see the illuminated trees without Saturday's crowds

Insider Tip: Friday evening is when locals do their Stroll shopping. Join them for a more intimate experience in stores offering wine, cider, and treats to browsers.

Saturday, December 6: The Main Event

This is what you came for—Stroll Saturday delivers holiday magic from dawn to well past dusk.

Morning (9:00 AM - Noon)

• 9:30 AM: St. Paul's Christmas Market opens with handcrafted gifts and baked goods
• 10:00 AM: Christmas Stroll Marketplace launches at the Stop & Shop parking lot—browse 50+ vendors featuring local artisans, food trucks, and nonprofits
• 10:00 AM: Climb the First Congregational Church tower for spectacular island views (open until noon)
• 11:50 AM: Town Crier rings in the official start of Christmas Stroll

The Moment Everyone Waits For

12:00 Noon: SANTA ARRIVES! Watch from Straight Wharf as Santa and Mrs. Claus dock via Coast Guard vessel. Follow the parade as they travel up Main Street in a horse-drawn carriage (or vintage fire truck) to the Pacific National Bank, where children can share their wish lists.

Afternoon (12:00 PM - 5:00 PM)

• All Day: Festival of Trees at the Whaling Museum
• Main Street Stage: Live performances by Theatre Workshop of Nantucket, Nantucket High School Choir, and more
• 2:30 PM: Ugly Sweater Contest at the top of Main Street (register at the Chamber table starting at 10:30 AM)
• Roaming Entertainment: Victorian carolers, the famous Talking Christmas Tree, and street performers

Evening

• Prime dining time: Restaurants offer special prix fixe menus and holiday cocktails
• After dinner: Pop into shops for end-of-season sales and holiday treats

Sunday, December 7: The Sweet Finale

A gentler day perfect for catching what you missed and creating final memories.

• Morning: Farewell brunches at island restaurants (The Nantucket Hotel's Sunday Brunch is legendary)
• 3:00-6:00 PM: Skate with Santa at Nantucket Ice Community Rink—complete with hot chocolate, food trucks, and live music
• All Day: Last chance for Festival of Trees and shopping

The Must-See Attractions

Festival of Trees at the Whaling Museum

This is Stroll's crown jewel. The Nantucket Historical Association transforms the soaring Great Hall into a forest of 75+ Christmas trees, each decorated with wild creativity by local businesses, schools, artists, and nonprofits. Past themes have included everything from "Under the Sea" with mermaid ornaments to trees made entirely of lobster buoys.

General admission includes both the spectacular decorations and access to the museum's world-class whaling exhibits. Budget at least 90 minutes—you'll want to vote for your favorite in the People's Choice Award.

The Christmas Stroll Marketplace

Saturday's outdoor market (10 AM - 3 PM) brings together the island's best artisans, food vendors, and nonprofits in one festive location. Find one-of-a-kind gifts, sample local treats, and warm up with hot cider. This is where you'll find official Stroll merchandise, including the coveted annual Stroll scarf that sells out quickly.

Holiday House Tour

Select historic homes open their decorated doors for tours (tickets required). This rare glimpse into Nantucket's architectural treasures, dressed in holiday finery, offers Instagram-worthy moments at every turn. Tickets often include Festival of Trees admission.

Photographic Moments You Can't Miss

• Brant Point Lighthouse: Adorned with an enormous wreath and red bow, this is Stroll's most iconic photo opportunity. Visit at sunset for magical light.
• The Rowboat Christmas Tree: Find this Nantucket original at Old North Wharf and Easy Street—a Christmas tree standing tall in a weathered red dinghy.
• Main Street Overview: Climb to the widow's walk at the Congregational Church (Saturday 10 AM - Noon) for the ultimate aerial view of decorated downtown.
• Flowers on Chestnut: This shop becomes a wonderland of lights, decorations, and floral arrangements—step inside for sensory overload in the best way.
• Window Displays: Local artists hand-paint holiday scenes on shop windows. Lemon Press traditionally features work by Meredith Hanson.

Shopping: End-of-Season Sales Meet Holiday Magic

Stroll weekend marks many shops' last hurrah before winter closure, meaning serious markdowns on summer merchandise alongside holiday offerings.

Can't-Miss Shops:

• Murray's Toggery Shop: Home of the original Nantucket Reds
• Nantucket Looms: Locally made textiles and weavers at work
• Current Vintage: Curated vintage finds with island flair
• The Toy Boat: Enchanting toys and books for all ages
• Sweet Inspirations: Nantucket's candy paradise

Pro Shopping Strategy: Buy summer items now at 40-70% off for next year, and remember—no sales tax on clothing in Massachusetts!

Dining During Stroll: Book Now or Forever Hold Your Peace

Restaurants embrace Stroll with special menus, festive cocktails, and decorations that rival the North Pole. Reservations are absolutely essential—many book up weeks in advance.

Stroll Dining Favorites:

• Brotherhood of Thieves: The island's legendary tavern transforms into holiday central with their famous Mudslides, hearty fare, and live music that captures Stroll's festive spirit perfectly
• Billie's: Upscale comfort food and craft cocktails in a cozy setting—their Stroll weekend specials are not to be missed
• Straight Wharf Restaurant: Opening specially for Stroll 2025—expect crowds and incredible atmosphere
• The Nantucket Hotel: Multiple venues from casual (Breeze) to celebration-worthy
• Lola 41: Sushi and cocktails with unbeatable energy
• Ventuno: Cozy Italian perfect for warming up
• The Gaslight: New American with stellar cocktails
• Brant Point Grill: Those views, those Bloody Marys

Budget-Friendly Options:

• The Green: Exceptional coffee and breakfast
• Provisions: Gourmet sandwiches and soups
• Straight Wharf Fish Market: Casual seafood counter service

Entertainment Beyond the Streets

• Theatre Workshop of Nantucket: Presenting Elin Hilderbrand's "Winter Street" (November 21 - December 7)—the perfect Nantucket story for Stroll weekend.
• The Dreamland: Special concerts and events, including potential surprise performances by touring musicians who love playing intimate island venues.
• Nantucket Performing Arts Center (formerly White Heron Theatre): "It's a Wonderful Life: A Live Radio Play" performances throughout the weekend in their newly renovated space.

Weather & What to Wear

December on Nantucket means:

• Average temperatures: 35-45°F
• Wind chill off the harbor makes it feel colder
• Possible rain, snow, or pristine clear skies

The Stroll Uniform:

• Warm, waterproof boots (cobblestones + potential ice = treacherous in heels)
• Layers, layers, layers
• Your finest/ugliest holiday sweater
• Hat and gloves (you'll be outside more than you think)
• That Nantucket Stroll scarf everyone's wearing

Making the Most of Your Stroll

• Book Early, Book Everything: Ferries, accommodations, restaurant reservations, and house tour tickets all sell out. Many visitors book next year's room before leaving the island.
• Embrace the Pace: Stroll isn't about checking off attractions—it's about soaking in the atmosphere. Duck into a shop for cider, chat with carolers, watch children's faces when Santa arrives.
• Mix Planned and Spontaneous: Have dinner reservations and must-sees, but leave room for discovering that perfect tiny gallery or joining an impromptu carol sing-along.
• Consider Staying Through Monday: Sunday evening, after day-trippers depart, the island exhales. You'll have downtown virtually to yourself for one last magical evening.

Why Stroll Captures Hearts

In an era of Black Friday chaos and Amazon algorithms, Christmas Stroll offers something real: a community celebrating together, merchants who know your name by weekend's end, and the kind of holiday spirit that makes cynics believe in Christmas magic again.

Whether you're escaping city stress, creating family traditions, or simply seeking somewhere that feels like a snow globe come to life, Nantucket's Christmas Stroll delivers. Just ask the thousands who return year after year, many now bringing grandchildren to experience what their own children fell in love with decades ago.

Ready to experience the magic? The 51st Annual Christmas Stroll takes place December 5-7, 2025. Start planning now—Nantucket is waiting to welcome you home for the holidays.