29 Nov 2019

LRE’s Guide to Nantucket Christmas Stroll

Nantucket Christmas Stroll

It is the most wonderful time of the year, especially on Nantucket because the annual Christmas Stroll is just around the corner! During the month of December, Nantucket is turned into the quintessential New England Christmas village. There is something truly magical about Main Street during the holidays. Read on for Lee Real Estate’s Guide to the Perfect Christmas Stroll:


Where to Eat


This elegant Italian spot is always one of our go-to’s, especially on their last weekend of the season. From perfect pasta to savory seafood, the menu at Ventuno is always excellent, and this is a great spot for island nightlife as well.

Via Mare

The atmosphere at Via Mare is quintessential Christmas Stroll. Cozy, comfortable, and a menu that makes it hard to choose just one dish – luckily, they offer small plates so you can experience a little bit of everything.


Looking to dine outside of town? Seagrille is an excellent choice for dining without battling the throngs of downtown on this busy December weekend. Not to mention the food is always top-notch.


If you left Columbus Weekend feeling sad about having your last CruComber of the season, now is the time to rejoice! Cru is re-opening for Christmas Stroll weekend, giving us truly one last chance to indulge until 2020.
Christmas Stroll Apres Ski Party

Straight Wharf

While you’re down at the wharf, be sure to stop by another one of our favorites who are also re-opening their doors for the occasion – Straight Wharf is perfect for an elegant dinner and is one of the island’s best nightlife locations for after dinner drinks!


Where to Shop

Earth Pebbles Pop-up at Susan A. Lee Gallery

Susan A Lee Gallery is hosting Gemologist, Rebekah Anderson with Earth Pebbles Gemology for a special Christmas Stroll Trunk Show.  Rebekah proudly represents fine estate and one of a kind gems and jewelry pieces, with something for every budget.
Trunk Show dates:  Friday-Sunday, December 6, 7 and 8.  10:00 a.m. to 5:00 p.m.


Stop by Quidley & Company while strolling this weekend to place your bids on a number of works by local artists. This annual art show begins on Thursday December 5th at Noon, and proceeds benefit both the Marla Ceely Lamb Fund and PASCON.

Christmas Stroll Craft Show

The Annual Christmas Stroll Craft Show at 11 Centre Street is always one of LRE’s favorite stops on Stroll Weekend. With the largest collection of handmade items on Nantucket all in one place, it is the perfect place to do some holiday shopping in addition to supporting local artists and artisans!
Christmas Stroll Craft Show

Basket Festival and Sale

This once a year extravaganza features the work of local weavers, carvers, woodworkers, and museum members. It is your only chance to see the work of so many contemporary basket artists for sale in one place.

Red Tickets

When strolling around town, be sure to visit local businesses participating in the Holiday Red Ticket Program. For every $25 spent, you’ll get a red ticket for the annual drawing on Christmas Eve for a chance to win either a $1,000 or $5,000 prize!

What to Do

Festival of Trees

Kicking off Stroll Weekend, the Festival of Trees transforms the Whaling Museum into a winter wonderland featuring community crafted trees throughout the entire museum. Local businesses, non-profit organizations, artists, and children design and display their trees for all of December.

Winter Walk(s)

Spend some time outside of town strolling through nature with the Nantucket Conservation Foundation. Christmas Stroll’s Winter Walk features the Masquetuck trail, highlighting the shores of West Polpis Harbor. This event is free and open to the public, but space is limited so it is recommended to register ahead on the Conservation Foundation website.

Book Signings

If you are an avid reader, head over to Mitchell’s on Saturday December 7th for a day full of book signings with some of our favorite Nantucket authors.

Sip, Script, & Stroll

Kick off Stroll with an evening of crafting! Learn the art of modern calligraphy and get ready to script everything from gift tags to cards to formal invitations. Tickets include all supplies, as well as light appetizers and holiday libations. Sign up here.
Christmas Stroll Crafts

A Nantucket Christmas Carol

Head to the White Heron Theatre for this holiday classic with a Nantucket twist! This adaptation of the Charles Dickens story features whaling captain Ebenezer Scrooge accompanied by music, drama, and quick-change artistry to help bring the tale to life!
Christmas Stroll Play - A Nantucket Christmas Carol

Santa’s Arrival

Christmas Stroll weekend wouldn’t be complete without a visit from Ol’ Saint Nick! Head to the Straight Wharf dock at 12:15 to welcome Santa in via Coast Guard Cutter, and join the parade up Main Street to have your photo taken and tell Santa your Christmas wishes!

Santa's Christmas Stroll Arrival

Photo Credit: Blog

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