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What You Need to Know About Nantucket Stroll Weekend


Nantucket Living

Marleah Lydon
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Here at Fisher Real Estate, we have a BIG problem…we just can’t decide what time of year on Nantucket is our absolute favorite! It could be Daffodil Festival weekend or maybe the hustle and bustle of July and August? We cherish the months of September and October when the crowds have thinned but the weather is still fantastic. And then there is Thanksgiving in all its Turkey plunge and tree lighting splendor? But let’s not forget about the last contender before we wait again for the daffodils to bloom; Nantucket Stroll!

nantucket stroll
Photo: Cary Hazelgrove


Stroll on Nantucket began years ago just as an attempt to get locals to stay on Nantucket to do holiday shopping rather than hop on the boat and head to the mainland in search of better deals. It consisted of shops staying open extra late and treating their loyal shoppers with hot beverages and maybe even an adult libation or two. Now, Stroll has expanded to a full weekend of festive fun for everyone to enjoy and not only keeping local Nantucketer’s here to shop but bringing tourists from near and far to join in on the fun. There is no better place to get excited for the holidays than our beautiful island 30 miles out to sea. Take our quintessential cobblestoned streets and line them with beautifully lit trees, and shops and offices that take the time to make their windows scream “winter wonderland” and you have yourself the perfect recipe for a weekend full of holiday fun.

Nantucket Stroll
Photo: Cary Hazelgrove


If you are lucky enough to be coming to the island for this weekend, you most likely already know where to go and when, and you hopefully already have reservations.  Cru and The Pearl are two of our office favorites that will reopen JUST for this special weekend, and both of which have fun and special events on Sunday (The Pearl’s Bubbly Bash and Cru’s Super Closing Brunch) before they close up shop until Spring ’17. We also can’t get enough of our favorite standbys who thankfully keep us fed most of the year, like Lola 41, The Nautilus, and Oran Mor.

Don’t forget to check out the local shops for great deals, and unique gifts for your loved ones…or even yourself! If you have time in the midst of all of the shopping, eating, and imbibing, there is even more notable greenery to be seen at the Whaling Museum. Check out the Nantucket Historical Association’s Festival of Trees where you will find dozens of them beautifully decorated and adorned with unique nods to Nantucket and the festive season upon us. With so much to see and do, we recommend checking out the full schedule of events for Nantucket Stroll to help decide how to fill your weekend itinerary.

Nantucket Stroll
Photo: Cary Hazelgrove


But before you fill all of your time, let’s talk about the most important guest coming this weekend.  He will arrive in style with his wife on a Coast Guard Cutter. Head out to Straight Wharf on Saturday, December 3rd at noon. Greet the big jolly man with the town crier as he rings in Stroll and head straight up Main Street and down Center to take a special seat with him at the Jared Coffin House. That’s right, Santa and Mrs. Claus are making an extra special stop on Nantucket. Once again, they will be here to find out what the little ones want for Christmas and if they have been naughty or nice.  But before you go see him, come see Team Fisher! Right before he arrives, warm up with some coffee and a pastry and chat Nantucket Real Estate from 9am-11am.

And as always, if you miss out on Nantucket Stroll this year, there is always next year. Give us a call and we can set you up with a rental for your next visit. And tune into our Main Street Camera this weekend to see what all of the fuss is about, you may just catch a glimpse of Santa too!

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,