The Perfect Nantucket Stroll Weekend

Every December, The Nantucket Chamber of Commerce puts on its annual Christmas Stroll weekend. It’s a few days that feel like they’re straight out of a Hallmark movie. The town is covered in festive decor, Main Street is lined with individually decorated trees, businesses deck out their storefronts, and the whole island is abuzz with cheer. Stroll weekend is one of the biggest times for shops and restaurants to gross sales, so it’s a great time to support your favorite small brands and get all of your holiday shopping done.

If you’re coming from afar, you’ll probably want to fly into Boston and then take a Cape Air flight over to Nantucket. That’s the quickest way to get there. If you’re completely against the small planes (I definitely don’t love them,) you can drive to the Cape or New Bedford and take the Hyline, Seastreek, or Steamship Authority over but that will add quite a bit of time to your travels. If you’re fairly local, it’s pretty simple to hop on a ferry over to the island.

I like to have at least 2 full days at stroll- Friday and Saturday. That means I either fly in on Thursday and spend the night, or I take a red-eye Thursday night to get in by Friday morning. Friday might be my favorite stroll day as it’s festive, bustling, but not overly busy. Saturday is the most popular day for day-trippers so it’s a lot more crowded and most of the “main events” happen on Saturday. Shops and restaurants are still open on Sunday though, so if you’re looking for a festive time to go but want to avoid the crowds, Sunday is your day.

I’ve gone to stroll solo for the last couple years (but met up with lots of friends!) and stayed at The Faraway. It’s a centrally located, has perfectly appointed rooms, has a great restaurant (Sister Ship,) and a coffee and donuts cafe, Cymbal’s, every morning. Some of my favorite shops are located on the same street, and the rest are just a block or so away. The location is excellent. If you’re traveling with a larger group, check out my post here that details my favorite hotels on island and also consider renting a house.

If dining is important to you, make sure to make reservations far in advance! Restaurants book up quickly. Here’s a list of my favorite restaurants. I tried a new spot this year, Billie’s, which had excellent food and a beautiful atmosphere. I’ll be adding it to my list of restaurant recommendations. I also went to Ventuno, Or, the Whale, and Lemon Press for lunch, and Handlebar’s for seasonal coffee (the orange mocha was delicious!) If you’re not into planning far ahead, you can always pop into Rose and Crown for a casual meal or try your luck in the bar areas of restaurants.

Make sure to stop into my favorite stores and pop into any that look intriguing to you. There are so many wonderful businesses and creatives on the island that I love to support, including pop ups and market booths that come for stroll. Aside from shopping and dining, take a walk down to Brant Point Lighthouse to see it dressed up in its beautiful seasonal wreathe, see Santa come by boat onto the island and greet everyone along Main Street (especially if you have kids,) and pop into festive parties that take place every night (this year I went to a caviar and champagne party at Nantucket Magic, and an appetizers and dancing party at Ten Easy Street.) I always run into lots of friends which makes for the best impromptu stroll moments.