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THE CALM BEFORE THE (CHRISTMAS) STROLL: INSIDER TIPS FOR WINTER ON NANTUCKET


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The bustle of summer has finally given way to Nantucket's lesser-known season: one of calmness, serenity, and peace mixed with joy and anticipation for the holidays. October-December is one of the best times to experience Nantucket as the locals do, with fewer crowds, small town charm, and plenty of celebratory festivities leading up to the annual Nantucket Christmas Stroll.


CAN'T-miss cozy traditions on Nantucket

The weeks between our last charters in October and the end of the year are full of unique community traditions that rival summer activities on the island. Stores begin installing their holiday window displays, cafes and breweries begin serving up their seasonal beverages, and shops begin handing out their “red tickets” before the Christmas eve drawings.


Now that we’re entering November, below are just a few of our favorite ways to kick off the holiday season on Nantucket.


  1. THE FESTIVAL OF WREATHS AND FESTIVAL OF TREES

    Nantucket Historical Association's Festival of Wreaths starts Nov. 24th and goes until Nov. 29th, featuring a creative array of wreaths made by residents, local businesses, and other island organizations. This leads right up to the Historical Association’s Festival of Trees, transforming the Whaling Museum into a winter wonderland (starting Dec. 5th through the end of the month).


  2. TREE LIGHTING ON MAIN STREET

    Friday, November 28th is the island’s annual tree lighting ceremony, marking what many consider the official start of the holiday season! Anyone on the island won’t be able to miss the 150 trees illuminated along Main Street, or the sounds from our community carolers. The following day is Small Business Saturday – a perfect opportunity to support local businesses as you begin your holiday shopping.


  3. SCALLOPING SEASON IS ON!

    While perhaps not considered a ‘cozy’ activity, winter is prime time for island scalloping. The season started October 1st (for recreational scallopers; November 1st for commercial) and runs through the end of March. Scalloping is an age-old tradition on Nantucket, and many look forward to it as a peaceful way to spend time out in nature (with their delicious harvest as an added bonus, of course).



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your stroll survival guide

The island shifts gears quickly after Thanksgiving to prepare for the infamous Nantucket Christmas Stroll on Dec 5th, 6th, and 7th. To experience the Stroll the way the locals do, plan ahead!


  • wear your walking shoes and festival attire

    This will be the island’s 51st annual Christmas Stroll, with plenty of vendors set up in a classic European Christmas Market fashion. Plan to shop around for food, gifts, and other vendor merchandise. Don’t forget your holiday sweater!


  • catch live entertainment

    On Friday and Saturday (the 5th and 6th), try to grab a spot on Sailor's Valentine’s front porch (located at The Nantucket Hotel & Resort). There, you’ll enjoy live music, delicious cocktails and warm beverages, and a curated Stroll weekend menu. First come first serve!


  • Don't Miss Santa's Nautical Arrival

    On Nantucket, Santa arrives like most locals and visitors do: by way of the harbor. Keep your eyes on Straight Wharf during the Stroll weekend where you’ll witness his exciting, seasonal arrival.


  • Book early!

    Stroll weekend fills up fast, so book accommodations and meal reservations early. Below we’ve highlighted some of our favorite off-season/year-round dining options on the island.


Off-season dining highlights

Once you’ve taken photos of the island’s off-season beauty, leisurely walked the bluffs without summer crowds, and made your way down Main Street to peruse the festive decorations, it’s time to settle in for a meal at one of our favorite year-round restaurants:




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for those counting down the days until summer...

Despite the many fun events happening on the island this winter, the cold weather months are not for everyone. Although the water is chilly now (which Cold Turkey Plungers will soon confirm), you can still give the gift of sunshine and open water this holiday season! NBW accessories and gift cards make the perfect stocking stuffers for anyone dreaming of salty ocean air and days on the water next summer.




Gift cards never expire, allowing their recipients to choose any adventure they choose, whenever they’d like – be it a fishing trip, cocktail party, family outing, or sunset cruise. It’s a gift you can guarantee no one will want to return. And don’t forget about our NBW merch which gives the gift of warmth and style for their upcoming adventures! 


For anyone trying their best to brave through the winter months, know that there’s only 30 weekends between now and Memorial Day. 🇺🇲

 
 
 

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