Christmas Stroll

History of the Christmas Stroll

The Christmas Stroll began in 1973 as a simple way for Nantucket merchants to thank islanders for their year-round support. That first year, shop owners stayed open late on a December evening, offering hot cider and cookies to neighbors who strolled through town. What started as a modest local gathering has grown into the island's premier event, attracting thousands of visitors and becoming a cherished tradition for generations of families.

Over five decades, the Stroll has evolved while maintaining its small-town charm. The tree lighting ceremony, Santa's arrival by boat, and carolers in period costume have become time-honored traditions. Today, the weekend encompasses dozens of events, from house tours to the Festival of Trees, yet the spirit remains the same: celebrating community, tradition, and the magic of the holiday season in one of America's most beautiful settings.

For many families, Christmas Stroll weekend is an annual pilgrimage, with traditions passed down through generations. Children who watched Santa arrive on the Town Pier now bring their own children, creating memories that span decades. The Stroll represents everything Nantucket does best - preserving history while creating new traditions, welcoming visitors while honoring community, and celebrating with warmth and authenticity.

The Main Events

Christmas Stroll weekend packs an extraordinary amount of festivity into a few short days. Here are the highlights you won't want to miss.

Friday Evening Tree Lighting

The weekend begins Friday evening with the official tree lighting ceremony at the top of Main Street. Crowds gather as darkness falls, clutching cups of hot chocolate and listening to carols fill the crisp December air. The countdown begins, and when the lights illuminate the majestic tree, the entire crowd cheers. It's a moment of collective joy that perfectly sets the tone for the weekend ahead. Arrive early to secure a good viewing spot - the area around the tree fills quickly, and the best positions go to those who stake their claim an hour or more before the ceremony.

Santa's Arrival by Coast Guard Boat

Saturday morning brings the event that children (and adults) wait all year to see: Santa Claus arriving on Nantucket via Coast Guard vessel. The crowd gathers at the Town Pier, scanning the harbor for the first glimpse of Santa standing at the bow. As the boat approaches, cheers erupt and children bounce with excitement. Santa disembarks to greet the crowd before leading a festive parade through the streets to his throne in town. This uniquely Nantucket tradition - Santa arriving not by sleigh but by boat - perfectly captures the island's maritime character.

Carolers Throughout Downtown

Strolling carolers in Victorian-era costumes roam the cobblestone streets throughout the weekend, their harmonies floating through the air and adding an enchanting soundtrack to the festivities. You'll encounter groups on Main Street, outside shops, and at various corners downtown. Many wear period clothing that evokes Nantucket's whaling era history, creating scenes that look straight out of a Dickens novel. Take time to stop and listen - these talented singers are integral to the Stroll's magical atmosphere.

Shop Open Houses

The heart of the Stroll is, well, strolling - and specifically, strolling through Nantucket's festively decorated shops. Stores throughout downtown throw open their doors for holiday open houses, offering refreshments, special discounts, and beautifully decorated interiors. Shop windows become works of art, each competing to create the most enchanting holiday display. This is prime time for holiday shopping, with many stores offering Stroll-exclusive items and one-of-a-kind Nantucket gifts you won't find anywhere else.

Hot Chocolate and Treats

Warmth comes in many forms during Stroll weekend. Shops and restaurants throughout downtown offer hot chocolate, mulled cider, and holiday treats to strolling visitors. You'll find tables set up outside stores with steaming urns, bakers offering samples of gingerbread and cookies, and cafes doing brisk business in warm beverages. Part of the Stroll experience is stopping frequently to warm up, sample something sweet, and chat with fellow celebrants before continuing your wanderings.

Historic House Tours

Several of Nantucket's historic homes open their doors during Stroll weekend, offering rare glimpses into private residences decorated for the holidays. These tours, often benefiting local nonprofits, showcase the island's architectural heritage adorned in festive splendor. Tickets sell out quickly - many visitors book house tour tickets as soon as they're released, months before the event. The tours offer a wonderful way to step out of the cold while experiencing Nantucket's living history.

Festival of Trees

The Festival of Trees is a beloved Stroll tradition featuring dozens of beautifully decorated Christmas trees created by local businesses, organizations, and individuals. Displayed at a central location (typically the Nantucket Whaling Museum or another prominent venue), each tree reflects a unique theme - from traditional elegance to whimsical creativity. Visitors vote for their favorites, and trees are often raffled off to raise money for charity. It's a wonderful indoor activity when you need a break from the cold.

The Atmosphere and Magic

What makes Christmas Stroll truly special goes beyond any single event - it's the cumulative magic of experiencing Nantucket at its most enchanting. Picture this: cobblestone streets dusted with snow (or at least glistening with frost), every lamppost wrapped in greenery and lights, shop windows glowing warmly against the early December darkness, and the sound of carols mingling with laughter and conversation.

There's a special energy during Stroll weekend that's hard to describe but impossible to miss. Strangers smile and greet each other. Children point excitedly at decorated windows. Couples hold hands as they wander through the festively lit streets. The island, often quiet in winter, pulses with joyful life. Even longtime visitors who've attended dozens of Strolls describe feeling a fresh wave of wonder each year.

The pace is different too. Despite the crowds, there's no rushing. People linger outside shops, stop to watch carolers, duck into doorways to examine window displays. Hot chocolate is sipped slowly. Conversations happen. The modern world, with its constant hurry, seems to pause for this one magical weekend, allowing space for something increasingly rare: genuine, unhurried holiday joy.

What to Wear

The single most important thing to remember about Christmas Stroll: it's cold. Early December on Nantucket means temperatures typically in the 30s and 40s (Fahrenheit), with wind chill potentially making it feel much colder. The maritime location adds dampness that can cut right through inadequate clothing. But don't let that deter you - proper preparation makes all the difference between magical and miserable.

Layering Strategy

• Base layer: Thermal underwear or moisture-wicking layers are essential. You'll be outside for hours, and a good base layer is your foundation for warmth.
• Middle layer: Fleece, wool sweater, or down vest. Something that provides insulation while allowing some flexibility.
• Outer layer: A warm, wind-resistant coat is non-negotiable. Down parkas, wool coats, or technical outerwear all work - just make sure it blocks the wind.
• Accessories: Warm hat (you lose significant heat through your head), scarf or neck gaiter, insulated gloves, and thick socks.
• Footwear: Waterproof boots with good insulation. Cobblestones can be slippery when wet or frosty, so choose shoes with good traction. Fashion boots often aren't warm enough - prioritize function.

Pro tip: Hand warmers and toe warmers (available at most pharmacies and outdoor stores) can be lifesavers. Tuck them in your gloves and boots for hours of added warmth. And dress more warmly than you think you need - you can always step into a shop to cool down, but it's hard to warm up once you're truly cold.

Where to Stay

Here's the hard truth about Stroll accommodations: you need to book far in advance. We're not talking weeks - we're talking months, potentially a full year ahead. Christmas Stroll is the most popular weekend on Nantucket's calendar, and every bed on the island fills up. Regular visitors often book next year's accommodations before leaving from the current year's Stroll.

Accommodation Options

• Historic inns: Properties like the Jared Coffin House, Union Street Inn, and White Elephant offer full Stroll packages with included events and breakfast. These fill first.
• B&Bs: Nantucket's numerous bed and breakfasts offer intimate settings perfect for the cozy Stroll atmosphere. Many go above and beyond with holiday decorations and special treats.
• Hotels: The Nantucket Hotel, The Wauwinet, and Greydon House all offer Stroll packages. The Nantucket Hotel's downtown location is particularly convenient.
• Vacation rentals: VRBO and Airbnb properties can work well for groups but also book extremely early. Downtown locations command premium prices and availability.

Booking Strategy

• Start looking 9-12 months before Stroll weekend
• Be flexible on location - properties outside downtown are often easier to find
• Check cancellation policies and book anyway, even if plans aren't certain
• Sign up for waiting lists at sold-out properties
• Check for last-minute cancellations in November - they do happen
• Consider arriving Thursday and staying through Sunday for the full experience

Ferry and Travel Logistics

Getting to Nantucket for Stroll weekend requires advance planning, especially if you're bringing a vehicle. The island is accessible only by ferry or plane, and both fill up quickly for this popular weekend.

Ferry Service

The Steamship Authority operates year-round ferry service from Hyannis to Nantucket. For Stroll weekend:

• Traditional ferry: About 2 hours and 15 minutes. More spacious, runs in almost all weather. Vehicle reservations open 30 days in advance and sell out immediately for Stroll weekend.
• Fast ferry: About 1 hour. Passenger-only (no vehicles). More prone to weather cancellations but convenient.
• Booking strategy: Set an alarm for exactly 5:00 AM when reservations open. Seriously. Vehicle spots sell out within minutes.
• Alternative: Leave your car on Cape Cod. Parking is limited on-island anyway, and downtown Nantucket is entirely walkable during Stroll.

Flying

Cape Air offers year-round service to Nantucket from Boston, Hyannis, and other regional airports. JetBlue operates seasonal service from various East Coast cities. December weather can cause flight delays and cancellations, so build buffer time into your schedule.

Getting Around the Island

Once on Nantucket, you won't need a car for Stroll activities - everything happens in walkable downtown. Taxis and ride services are available for getting to/from the airport or ferry. If you're staying outside downtown, check if your accommodations offer shuttle service to town.

Best Spots for Tree Lighting

The Friday evening tree lighting is one of Stroll weekend's most cherished moments. Positioning yourself well can make the difference between an immersive experience and viewing over heads from the crowd's edges.

Prime Viewing Locations

• Top of Main Street: The tree stands at the head of Main Street near the Pacific National Bank. The closest spots offer an intimate experience but require arriving 1-2 hours early.
• Bank steps and surrounding area: Elevated positions around the Pacific National Bank provide slightly elevated views over the crowd.
• Upper Main Street shops: Some shops with second-floor windows offer views - inquire about special events or seating.
• Mid-Main Street: Standing partway down Main Street offers good views of the tree while allowing easier crowd navigation before and after.

Tips for the Ceremony

• Arrive at least an hour before the scheduled lighting time
• Bring something warm to drink and hand warmers
• Use the restroom beforehand - facilities become crowded
• Keep young children on shoulders for better views
• After the lighting, linger to enjoy the illuminated scene rather than rushing away

Dining During Christmas Stroll

Restaurant reservations during Stroll weekend are nearly as competitive as accommodations. The island's population swells significantly, and every dining room fills to capacity. Plan ahead or plan to eat creatively.

Reservation Strategy

• Make dinner reservations 4-6 weeks in advance for popular restaurants
• Book breakfast and lunch reservations too - they'll be busy
• Consider early (5:30 PM) or late (8:30 PM) seating for better availability
• Prepare backup options in case your first choices are full
• Hotel restaurants often reserve tables for guests - check when booking accommodations

Alternative Dining Options

• Casual spots: Places like The Brotherhood of Thieves, Fog Island Cafe, and local pubs often have shorter waits
• Takeout: Pick up sandwiches or pizza and enjoy them at your rental
• Bar seating: Many restaurants hold bar seats for walk-ins - be prepared to wait
• Special events: Some restaurants host Stroll-specific dining events or prix fixe menus

Don't Miss

• Hot chocolate at various shops and cafes throughout town
• Fresh-baked cookies and holiday treats from local bakeries
• Mulled wine and cider at restaurants with bars
• Special Stroll menus featuring seasonal New England fare

Shopping During the Stroll

Christmas Stroll is a premier holiday shopping experience. Nantucket's unique boutiques and galleries pull out all the stops, creating beautifully decorated spaces filled with one-of-a-kind gifts you won't find on the mainland.

What to Shop For

• Nantucket lightship baskets: The island's iconic craft, ranging from small ornaments to full-size purses. Many shops offer Stroll-special editions.
• Christmas ornaments: Nantucket-themed ornaments make wonderful keepsakes - scallop shells, lighthouses, whales, and island scenes.
• Local art: Galleries showcase island artists, with many offering holiday-themed works perfect for gifts.
• Nantucket clothing: The signature "Nantucket red" faded red clothing, plus cozy sweaters and maritime-inspired apparel.
• Specialty foods: Cranberry products, jams, chocolates, and other edible gifts from local purveyors.
• Home goods: Nautical decor, candles, linens, and coastal-inspired items for the home.

Shopping Tips

• Start early Saturday morning before crowds peak
• Return your purchases to your accommodations periodically to avoid carrying heavy bags
• Ask about shipping - many shops will mail purchases home
• Look for "Stroll Special" signs indicating limited-edition items
• Don't miss the side streets and upstairs shops - some of the best finds are off the main drag

Activities for Kids

Christmas Stroll is genuinely magical for children. The entire weekend feels designed to delight young visitors, from Santa's arrival to cookie decorating to the general wonder of a town transformed into a holiday wonderland.

Kid-Friendly Highlights

• Santa's arrival and parade: The main event for kids - watching Santa come to town by Coast Guard boat and then parade through the streets.
• Meeting Santa: After the parade, Santa sets up to meet children. Lines can be long, so plan accordingly.
• Cookie decorating: Various locations offer kids' cookie decorating activities throughout the weekend.
• Festival of Trees: Kids love voting for their favorite decorated trees and marveling at the creative displays.
• Carolers and performers: Street entertainment delights children of all ages.
• Shop windows: Exploring the decorated window displays is like a treasure hunt for kids.
• Hot chocolate stops: Frequent warm-up breaks with sweet treats keep spirits high.

Tips for Families

• Dress children in multiple warm layers - they'll be outside a lot
• Bring a stroller for little ones, though be prepared for cobblestone challenges
• Plan around nap times if possible - tired children miss the magic
• Let kids pick out a special ornament as a yearly tradition
• Book family-friendly accommodations with space to spread out
• Consider the earlier events (Friday tree lighting, Saturday morning Santa) to avoid late-night crankiness

Tips for Making the Most of It

After decades of Strolls, veterans have developed strategies for maximizing the magic while minimizing the hassles. Here's hard-won wisdom for first-timers and returning visitors alike.

Before You Go

• Book accommodations and ferry as far in advance as possible
• Make dinner reservations 4-6 weeks out
• Check the official Nantucket Chamber calendar for event schedules and times
• Purchase tickets for house tours and special events early - they sell out
• Pack warmer than you think necessary

During the Weekend

• Start early each day - morning crowds are lighter
• Take regular breaks to warm up in shops, cafes, or your accommodations
• Stay through Sunday if possible - it's less crowded but still festive
• Walk the side streets, not just Main Street, for a fuller experience
• Leave time to simply wander without a rigid schedule
• Talk to locals - they love sharing Stroll traditions and tips

Making It Special

• Create family traditions: same restaurant, same ornament shop, same viewing spot for tree lighting
• Take lots of photos but also put the phone away to fully experience moments
• Write in a travel journal or have kids draw pictures
• Buy a Nantucket ornament each year to build a collection
• Send postcards from the post office - the Stroll postmark is special