Nantucket Christmas Stroll has grown from a small holiday celebrations for island locals to a seasonal phenomenon and for many, a yearly pilgrimage. This year was my first time attending and although it was different from what I expected, it was magical.
How to Get There
Because Nantucket is an island you can, shocker, only get there by boat. There are two ferries from Hyannis, MA that take you there, the Hy-Line Cruises fast ferry (1 hour) and the Steamship Authority slower ferry (2 hours, 15 minutes). You can take a car on the Steamship ferry but you really won’t need one. I’d recommend taking the Hy-Line ferry. There’s a parking lot in Hyannis and a shuttle bus from the lot to the boat. Or, if you’re taking public transit, it’s a ten minute walk from the Hyannis Transportation Center (where busses from Boston come in) to the ferry terminal.
Where to Stay
The hotel is a crucial choice for Stroll. First of all, things book up way ahead of time so plan in advance. Many groups come year after year and book accordingly. I stayed at The Brant, one of my favorite hotels on the island. The Brant is perfectly situated for Stroll. It’s close enough to walk easily into downtown and to and from the ferry, but it’s distanced enough that you won’t be kept up by noise and revelry late into the night.
Amenities are another bonus of staying at The Brant. This year they hosted a lavish welcome party for guests complete with gourmet hors d’oeuvres and wine. They also always have a continental breakfast included and happy hour drinks available. The staff is incredibly lovely and they’re happy to assist with anything you need from restaurant recommendations to ironing boards.
What to Do
Shopping is a big deal at Stroll. The event was originally designed to give islanders opportunities to do their Christmas shopping without having to go to the mainland. Many shops only do one sale every year and it’s during Stroll. You’ll often find 50% off at pricey boutiques, so it’s a great opportunity to score some deals and find unique gifts for loved ones.
One of my favorite on-island shops is Four Winds, the oldest gift shop on Nantucket (and it’s still family run!). They have tons of great products including special Stroll sweatshirts and hats, Christmas-themed pajamas, and hand-painted ornaments by local artists. They’re also very active in making Stroll magical. For several years they’ve run this adorable hot chocolate truck, doling out free hot chocolate to folks as they come in on the ferry.
There are also many holiday markets popping up at this time. It’s really fun to stroll through the local vendors and meet artists, farmers, craftspeople, and more. I bought a bag of cranberries from a historic island cranberry bog that I made into garlands to use on my tree year after year.
Eating and drinking is another pastime of Stroll. In fact, it’s evolved into a bit of a scene. We noticed many ladies friend groups, all in matching holiday-themed outfits, enjoying themselves quite heavily at the cocktail bars. I wasn’t expecting a party scene but it was delightful to see everyone having so much fun.
I wrote a guide to Nantucket restaurants for Eater that you can check out, but some of my favorites are Ethos Wine Bar, Straight Wharf Fish, and if you’re feeling extra fancy, Via Mare. The donuts pictured above are sold at the Faraway Hotel, it’s a perfect spot to stop for a coffee and sweets break in between activities.
True to its name, the third most popular activity during this festival is to stroll downtown. Nantucket is already incredibly charming, but decked out for the holidays it feels like a Hallmark movie set. Christmas trees decorated by local children and shops line the cobblestoned Main Street, every store window is strung with lights and wreaths, and everyone is dressed for the occasion.
All in all, Nantucket Christmas Stroll is worth a visit even if you can only swing a day trip. It’s a special New England tradition that will get you into the holiday spirit like nothing else.