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Nantucket Christmas Stroll: Where To Eat, Drink & Be Merry!


Events & Traditions

Marleah Lydon
Nantucket Christmas Stroll

Tree Lighting

Follow these links for 2018 Blogs on Nantucket Stroll: 

Merry Nantucket Stroll 2018

Holiday Market and Craft Fair Guide

 Nantucket Christmas Stroll

It feels like just yesterday we were packing away bathing suits and paddle boards in preparation for school nights and jaw-dropping October sunsets. Now we find ourselves breaking out Santa hats, jingle bells, and our wish lists for Ol’ Saint Nick…Christmas Stroll is upon us!

Let’s not forget how we got here – over 40 years ago a few thoughtful merchants extended their shop hours and dished out some tasty treats and holiday libations in hopes to encourage locals to stick around for their Christmas shopping rather than hopping on the next ferry to spread their wealth across Cape Cod! If they could only see us now; not only do locals stick around for shopping and festive activities, but Nantucket Christmas Stroll attracts crowds from near and far that could rival August numbers (certainly not temperatures though)! If you are lucky enough to be joining us for this unforgettable weekend, your biggest problem is simply having too many activities and too many dining options to choose from. Have no fear, Team Fisher will highlight a few musts to make the weekend to-do list a little less daunting!

Food + Drink

Last year we told you about our two favorite stroll spots to eat and toast to the most wonderful time of the year- Cru and The Pearl. Unfortunately, neither will be joining in on the merriment this year, but as they say, when one door closes, another opens and Straight Wharf Restaurant is doing just that! For the first time in their 42 years, SWR will open their doors and fill a pretty sizable gap in wining and dining this year. This place is sure to draw a crowd while serving up cozy cocktails, plenty of champagne, an always mouthwatering bar menu, many impromptu dance parties, and even a Christmas market featuring some of our favorite small-town vendors!

Now just because SWR will surely be a new Nantucket Stroll favorite, let’s not forget our tried and true places to wine and dine! If you’re looking for a similarly upbeat and happening place to go, Team Fisher recommends Lola 41 for tasty sushi and a vibe that can’t be beat; Nautilus for Asian-inspired small plates and a super cool energy; or Proprietors for a farm-to-table menu perfect for sharing and a killer team shaking up creative craft cocktails behind the bar (if Sunday Brunch is on your mind, Proprietors is where you want to be!). Looking for a more subdued dining scene? Head to Oran Mor for a quieter setting that is still sure to knock your Christmas stockings off or reserve a seat at Le Languedoc for classic French cuisine with a delicious Nantucket influence.

If you’re just looking for somewhere to sip, be sure to check out our year-round favorite Cisco Brewery for live music, and tasty draughts and their twists on classics like Egg Nog and Hot Apple Cider or go see our friends at Epernay Wine & Spirits to stock up and for tastings all weekend long!

Theater + Entertainment

If you’re a fan of “The Band” and their many hits (think “Up on Cripple Creek”, “The Night They Drove Old Dixie Down”, “Ophelia”, and “The Weight”) you will be pleased to know that the ever popular “The Weight Band” will be making the trip over to our lovely Isle for Stoll, too! “The Weight Band” features former members of “The Band” as well as others deeply connected to the era and will be playing two spectacularly intimate shows at the Dreamland! Thursday night’s show sold out quickly, but if you hurry you just might be able to snag a couple of seats to Friday’s show! This is sure to be a special couple of nights, and local small business owner; James Lydon (largely responsible for making these exciting shows a reality on Nantucket), hopes to make this an annual tradition!

If live theatre is more of your cup of tea, don’t miss “It’s a Wonderful Life: A Live Radio Play” at White Heron Theatre with shows on both Thursday, Friday, Saturday, and Sunday! If you weren’t already feeling the holiday spirit, this American classic is sure to get you there. You can also get your fix at Theatre Workshop of Nantucket where they will feature one of the most popular musicals, “The Sound of Music” with shows all weekend as well!

If you’d rather mingle freely while still being immersed in a winter wonderland, don’t miss the Nantucket Historical Association’s highly anticipated Festival of Trees. See the Whaling Museum in a whole new light as it is transformed into a holiday haven filled with dozens and dozens of gorgeous trees decorated thoughtfully by local business owners, non-profit organizations, artists, and children. This stunning display of Christmas tree cheer is open to the public for a small admission fee on Friday, Saturday, and Sunday! Want that WITH food and drinks? Get on the waitlist ASAP for the eat, drink, and be merry version of the Festival known as the “Preview Party,” held on Thursday night. (or put a reminder in your calendar to make sure and snag a few tickets for next year)

For the Kids!

It wouldn’t be Stroll without a visit from our favorite jolly man in a red suit – Santa! To really kick off the weekend meet the Town Crier and Santa at Straight Wharf and follow him to the Jared Coffin House so your kids can let him know if they’ve been naughty or nice and what is on their list for the big day on December 25th!

While maybe not quite as famous as the big guy, don’t miss a chance to meet Barnaby Bear! Meet the author of our favorite Nantucket children’s book series at a book signing in Barnaby’s Place, the kids’ cafe in Nantucket Bookworks with a special appearance by Barnaby from 11 to 11:30 am on Saturday. And, of course, we know the kids need to eat, too! Family friendly dining options can be found at the old-fashioned soda fountain at Nantucket Pharmacy, The Brotherhood, Back Yard BBQ, and the famous, all you can eat Sunday Brunch buffet at The Brant Point Grille complete with a special “Kid’s Corner” and live music!

Just Strollin’

Nantucket Christmas Stroll

If itineraries full of activities and reservations aren’t your speed, just get here! The streets of downtown Nantucket are adorned with hundreds of brightly lit Christmas trees, and the sound of strolling carolers ring throughout. With dozens of shops and galleries (featuring incredible end-of-year sales!) to duck in and out of, and the always popular Christmas Stroll open air market held at the foot of Main Street, you certainly won’t have a problem getting in the holiday spirit and checking items off your Christmas list!

We hope to see you on Main Street to check in on the Nantucket Real Estate market, book your rental for your next dreamy Nantucket getaway, or just to say hi and share in the holiday cheer!

Nantucket Christmas Stroll

Written By

Marleah Lydon

Marleah loves the Nantucket lifestyle and takes advantage of as many aspects of it as possible. When she is not at the office, you can find Marleah fishing,