Off the Beaten Path: Peaceful Ways to Enjoy Nantucket Stroll Weekend

Nantucket Stroll takes place December 5-7, 2025, and is one of the island’s most beloved holiday traditions—a festive, glittering kickoff to December filled with twinkling lights, Santa sightings, and shopping along the bustling downtown streets. But if you love the spirit of Stroll without the shoulder-to-shoulder crowds, you’re not alone. Luckily, there are plenty of ways to soak in the island’s winter beauty while keeping the experience slower, quieter, and more intentional.

Here are some off-the-beaten-path ideas to help you savor the magic of Stroll Weekend—without the overwhelm.

1. Catch the Quiet: Arrive in Town Before the Crowds

One of the simplest ways to enjoy Stroll’s festive atmosphere is to get an early start. Before the ferries dock and the sidewalks fill, town is peaceful and picture-perfect. Sip a coffee, admire the wreaths and window displays, pop into a few shops right as they open, or simply stroll the cobblestones while everything feels fresh and calm. Our office is always open if you would like to stop by!

Fisher Tip: Walk around town on your own time and vote at nantucketchamber.org/vote for the best decorate storefront, and your favorite decorated downtown Christmas tree.

2. Trade the Streets for Sand: Take a Winter Beach Walk or Drive

While everyone else clusters around Main Street, the beaches are gloriously empty. Bundle up and head to Steps Beach, Jetties, Miacomet, or Madaket for a brisk walk along the shoreline, or drive onto Nobadeer, 40th, or Cathcart. In winter light, the ocean looks moodier, the dunes feel wilder, and the sounds of the waves offer a quiet counterbalance to the holiday buzz.

3. Candlelit Comfort: Order Takeout & Stay In

Who says Stroll has to be spent entirely in town? Order takeout from one of your favorite island spots and enjoy a cozy night in. Light candles, throw on a holiday playlist, and turn your rental or home into your own private retreat. It’s a beautiful way to unwind after a day of festivities—and a welcome escape from long restaurant waits.

4. Dine Outside Downtown

If you love a great meal but not the lines, head to restaurants outside of the busy core. Mid-Island you will find gems that fly a bit under the Stroll radar. Dining beyond downtown is a way to support local businesses while enjoying a fun atmosphere.

5. Choose Experiences With a Cap: Opt for Ticketed Events

Ticketed events—whether it’s a holiday concert, tasting, workshop, or gallery event—often have limited capacity, guaranteeing a more comfortable experience. They’re the perfect way to stay festive while ensuring your Stroll weekend feels manageable and intentional. Options include the Friends of Nantucket Public Schools Holiday House Tour, the Nantucket Stroll Bash at Straight Wharf Fish, tour the Historic Mansions of the Cliff and Brant Point, Frog & Toad the Musical, or the Festival of Trees.

6. Explore Nature Trails & Hidden Corners

Beyond the beaches, Nantucket’s conservation trails are serene and magical this time of year. Head to Sanford Farm, Masquetuck, or Millbrook for quiet paths, open skies, and that fresh winter air. You’ll feel miles away from the bustle, even if you’re only minutes from town.

7. Enjoy the Lights After Dark

If you want to see downtown lit up without the daytime crowds, come back after dinner. Once the day-trippers head home, Main Street takes on a slower, softer glow. The Christmas tree, shop windows, and garlands feel even more magical at night—and the streets are blissfully walkable.

8. Shop Early (or Late in the Weekend) for a More Relaxed Experience

If shopping is on your Stroll agenda, consider browsing local boutiques on Wednesday, Thursday, or Sunday. These days are noticeably quieter than the peak Stroll rush on Friday and Saturday, when the downtown sidewalks fill quickly and lines form outside popular shops. Visiting just before or after the main festivities lets you enjoy beautifully decorated storefronts, chat with shop owners, and take your time selecting gifts—without feeling swept along by the crowds. 

9. Visit the Brant Point Lighthouse Wreath for Harbor Views

The iconic Brant Point wreath is a must-see during Stroll Weekend—and the best part is that there’s plenty of room to spread out. Instead of squeezing through downtown crowds for photos, head to the lighthouse where the harbor opens up around you. It’s peaceful, scenic, and perfect for a quiet moment. Watch the boats, take in the sweeping views, snap your holiday photo, and enjoy one of Nantucket’s most beloved traditions with lots of fresh air and room to breathe. 

A Slower Stroll

Stroll Weekend doesn’t have to mean crowds, packed sidewalks, or rushing around. With a little creativity and intention, you can enjoy the best of the season—twinkling lights, festive energy, and Nantucket’s winter charm—while still savoring peace and space.

Whether you’re wandering the shoreline, exploring quiet trails, or enjoying dinner by candlelight, these off-the-beaten-path ideas offer a chance to experience Stroll in a way that feels relaxing, joyful, and uniquely your own.