Written By: Leise Trueblood

Lace up your walking shoes and dig out your favorite ugly Christmas sweater – it’s time for Christmas Stroll!

Ahh, the beloved Christmas Stroll. What once began as a simple way to keep locals from doing their Christmas shopping on the mainland has grown into a 3-day Island-wide holiday extravaganza. It’s a favorite for all ages and a true Nantucket original. From seasonal markets to festive beverages, we’ve got the full lowdown on how to stroll the weekend away the right way.

1. Friday: Bring the right gear

If you’re making the trek up to the rock on Friday, make sure to bring the Christmas Stroll essentials. These include (but are not limited to) comfortable walking shoes, warm gloves and hats, festive sweaters and holiday garb. If you’re a newbie to Nantucket, the cobblestones will really put a bump in your plans to wear high heels or stiletto boots, so leave those at home and bring sturdy, comfortable shoes to stroll in style. Bonus points if you don something in Nantucket red, or if you happen to have a Christmas sweater that lights up.

2. Saturday Early Morning: Eat a healthy breakfast

Stroll is a marathon, not a sprint! Prep for the day’s activities with a healthy breakfast from a local eatery. For a full pancakes-eggs-and-bacon breakfast, Fog Island Cafe is your best bet. Doughnuts at the Downyflake are a popular go-to, but for croissants and morning buns stroll over to Wicked Island Bakery. For smoothie lovers, head to The Green or Lemon Press. Looking for a cozy spot to read the paper and enjoy a cup of coffee? Corner Table at the Nantucket Culinary Center boasts comfy banquettes and a quiet place to enjoy your read. After you’ve gotten your protein and your caffeinated fuel, you’ll be ready to get the ball (st)rolling.

3. Saturday Mid Morning: Let the strolling begin!

Now that you’re dressed the part and ready to start the day, head to Main Street to take in all the magic that is Christmas Stroll. The town crier will officially ring in the weekend at 11:45, followed by Santa’s arrival on Straight Wharf. We recommend starting there and working your way up Main Street, stopping in to as many shops as you like. Can’t-miss events? The People’s Choice Award for Best Storefront and Tree Decorations at 10:00 am, book signings at Mitchell’s and Bookworks, and the Holiday Marketplace in the Stop & Shop parking lot. Expect sales, cookies, and a few adult beverages to be offered along the way – but like we said, this is a marathon, not a sprint! Make sure to take time to hydrate as the day goes on. Expert Pro Tip: bring a hydration backpack with water to help wash down all the hot cocoa and champagne.

4. Saturday Afternoon: Take a break at the Brewery

Speaking of beverages, you’re going to want to try the holiday hot drinks at Cisco Brewers this weekend. …What’s that you say? Isn’t the brewery outdoors, chilly, and only for cold beer? Not this time of year! The favorite local watering hole will provide a tent, heat, and delicious spiked eggnog for Stroll weekend. You can also enjoy tunes from various bands playing throughout the day, and new exclusive Cisco Stroll merch! Be sure to get there on the earlier side – even without the summer crowds, there is usually a line (and a cover) by mid-afternoon.

5. Saturday Night: It’s all about the entertainment

There’s no wrong way to get into the holiday spirit this weekend, and there’s a slew of entertainment avenues to satisfy even the toughest of holiday grinches. Feeling artsy? Take in a performance of TWN’s Miracle on 34th Street or White Heron Theatre Company’s A Nantucket Christmas Carol. Looking for a long, relaxing, delicious dinner? Check out the list of open restaurants for Stroll here – many reopen just for this special weekend, and feature one-time-only menu offerings. If you’re looking to paint the town red and sing holiday songs at the top of your lungs, jam out at Club Car or the Box.

6. Sunday: The savvy way to sign-off from Stroll

As you wrap up your Stroll festivities, make sure to ski over to CRU‘s Apres Ski Brunch on Sunday afternoon. Known as one of the best holiday parties of the year, guests and staff alike will be decked out in retro ski suits, wild winter wear, and exclusive Cru Stroll t-shirts. Make sure to wear your comfortable shoes again because the dance floor will be lit up with tunes from DJ Ryan Brown! Looking for something a little more laid-back? The Nantucket Hotel will be hosting an a la carte brunch with live music, and the Whaling Museum will present a recital of Nutcracker dances from the Nantucket Ballet. All fun and festivities aside, getting off this treasure island can be tricky with winter weather in the air, so be sure to keep an eye on the ferry alerts. But don’t be afraid of getting stuck – you’ll just have to keep strolling a little while longer!

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