The Insiders Guide to the Nantucket Christmas Stroll

Nantucket Christmas Stroll / Nantucket Chamber of Commerce

Nantucket Christmas Stroll Weekend is December 1-3, 2017

While most people think Santa is spending time readying his sleigh for Christmas, the rest of us know he is prepping his BOAT for a weekend filled with holiday activities on Nantucket!

The first Nantucket Stroll was 44 years ago and has grown into a winter tradition for islanders, Cape Coddder and hearty New Engenders alike! With it’s overwhelming popularity, comes the difficulty of how to approach this weekend event if you are a new comer.

With the help of Betsy Rich (from Hy-Line) and the Nantucket Chamber of Commerce, we have a few tips and tricks and insider information along with helpful links so you can plan out your holiday weekend.

Nantucket Christmas Stroll / Nantucket Chamber of Commerce

Getting There: Nantucket is an Island after all. You are limited to transportation by water or air. No matter if you take Hy-Line, Steamship or fly with Cape Air, it is imperative to make advanced reservations as most all trips sell out. Christmas Stroll is one of the top three busiest weekends all year!

Staying There: What a treat it is to stay for the weekend or an overnight, and not just the day! What you need to know is that a lot of accommodations require a two-night minimum stay. The best source of available accommodations is Nantucket Accommodations It’s one stop to find out about availability for the entire island.

Getting Around: All the events are downtown, so everything’s within walking distance! If you choose to fly to the island, please note that the airport is not downtown so you will need taxi service.

Sightseeing: Nantucket Island Tours is operating ‘Stroll Holiday Cheer Tour’ on Saturday at 3:00pm. This tour will give visitors a historic and fun tour of Nantucket dressed up for the holidays. Tickets are available for purchase with Hy-Line ferry tickets. Space is limited.

What to Wear: I cannot stress enough the importance of dressing for the weather, and comfort. There are many people who enjoy wearing their holiday best; but it’s December in New England which can mean just about anything. Also, the cobblestoned Main Street can be a challenge to navigate in even the most comfortable, and even-keeled shoes.

Nantucket Christmas Stroll / Nantucket Chamber of Commerce

Favorite Events:

Annual Festival of Trees the Nantucket Whaling Museum, all weekend

Historic Walking Tour, all weekend

Town Crier rings in Christmas Stroll, Saturday at 11:45am – top of Main Street

Santa & Mrs. Claus arrive by Coast Guard vessel, Saturday at 12:30pm – Straight Wharf

For a complete listing of events:


About Cat Wilson

Cat Wilson is "That Girl" on Cape Country 104 – a Cape Cod native and longtime Cape radio personality. She is a passionate supporter of Military and Veteran causes on the Cape and also hosts local music spotlight program, “The Cheap Seats” on Ocean 104.7.
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