What is Nantucket Stroll? (and how to have the best time!)
Samantha, Eldest & Co founder, here. If you know anything about me, besides that I’m an eldest daughter, it’s probably how much I love Nantucket. I’ve spent every summer of my life there (and for the past 5 years, more like 3-5 months a year there) but there is one weekend that holds a really special place in my heart: Christmas Stroll.
When most people think about Nantucket, they think about New England summer - which is fabulous. Sea air, coastal grandmother outfits, lobster rolls near the water, what’s not to love. But Nantucket is a year round community and after the summer crowds have gone there are still a variety of magical times to be on island before the true winter doldroms set in.
Being that my birthday is near Christmas, I’ve always been a big Christmas person. So when I discovered that there’s a weekend that blends Nantucket and Christmas - of course I was sold. But there’s a lot of questions around this weekend so let’s discuss…
What is Nantucket Stroll?
Let’s set the scene for you. Nantucket’s Christmas Stroll is a delightful holiday weekend celebration that takes place on the island of Nantucket, typically the first weekend in December, a.k.a. the weekend after Thanksgiving. Imagine a small-town Gilmore Girls vibe meets grey shingled New England beach town, all wrapped in festive cheer. Or for those TSITP fans, just imagine those times that Conrad and Belly ended up in Cousins over Christmas. In real world Nantucket, it’s a time when shops reopen for one last sale before closing for the off-season, the streets are decorated and the spirit of the season is palpable. Because many families are still recovering from the whirlwind of Thanksgiving and kids being off school the week prior, this weekend more than others in the fall tends to swing toward adults and as such, makes for a great couples trip or getaway with friends.
What to expect at Nantucket’s Christmas Stroll
Christmas Stroll (or Stroll for short) is not just about the decorations, there’s activities abound. In town on Saturday and Sunday, you’ll have the majority of stores open with sales running and often little pop ups with drinks or treats. On Saturday around noon, you’ll notice a swell of people as Santa arrives in via the Coast Guard around noon and parades up Main Street accompanied by many a costumed participant. If there are kids on island, this is when you’ll see them, but honestly even as an adult it’s fun to watch.
While you’re in town, they host a local market, usually in the Stop & Shop parking lot, with fresh food and goodies. Worth a stop before or after Santa has come in.
In the evenings, the food and drink game is everybody’s focus - restaurants are often featuring specialty menus and festive additions so make sure you plan your meals ahead of time since everybody will be very busy - for most restaurants, Stroll is even busier for them than peak weekends in August.
How to plan your visit to Nantucket for Stroll
Before you start packing your bags, let’s talk logistics. Traveling to Nantucket during this time can be a bit of a challenge. The direct flights from Chicago, DC and New York have usually ended by this time of year so those coming from far away will need to connect through Boston. There are regional flights on Cape Air but these can get expensive and fill up quickly.
Most people rely on the ferries, which are more affordable and a bit more weather resilient than flights but unlike a normal day, you do need to book tickets ahead of time for these boats given the demand. It’s essential to plan ahead, especially if you have specific travel dates in mind. Keep in mind that winter storms can be unpredictable, so if you have a must-make meeting on Monday, it might be wise to rethink your travel plans for that weekend.
Nantucket Stroll is a highly popular event, and it’s not the best time to attempt to save a few bucks by booking last minute. This is a high demand weekend so definitely plan everything - accommodations, travel, and reservations well ahead of time.
Where to stay on Nantucket during Stroll
When it comes to accommodations, you’ve got options. You can book any of the lovely hotels or B&B’s in town, which make for easy walking to the festivities. But if your group size is more than 2, it’s also worth considering renting houses for the weekend, so you can have a little more space and/or have the option to have one meal at home if you want. Local real estate agents can help you reserve (I am actually a licenses Massachusetts real estate agent so if this appeals to you, DM me on my real estate Instagram @nantucketyall and I’d be happy to help). If you’re not going to have/rent a car, staying in the town district will definitely be your best bet!
What to do during Stroll
Once all the logistics are handled, let’s talk a bit more about the itinerary. We’ve already talked Santa’s arrival. It’s a beloved tradition that kicks off the festivities. Make sure to explore the local shops and take advantage of the holiday sales.
The other don’t miss activity is the holiday vibes at Cisco Brewers. A local institution, the brewery is about 15 minutes from town via car and is always fun this weekend, well decorated and buzzing with crowds. You can cab/uber there or there’s also a free shuttle that runs from Federal Street out to Cisco and back for those without a car.Try a spiked cider or one of the island-exclusive beers on tap you can’t get anywhere else and enjoy the live music and festive energy.
Dining wise, let me say it again: don’t leave reservations to chance. They usually open up mid/late October and restaurants will be fully booked. You can usually find options at some of the less popular spots but my favorites like Ventuno, Via Mare, Proprietors, Oran Mor, and Or The Whale fill up fast! Make sure to book your table early.
After dinner, if you still have the energy (I’m usually bee-lining for my cozy bed), there’s a fun, festive nightlife scene for keeping the holiday spirit alive into the evening. Head over to Club Car (which is normally wrapped like a present and features a live kareoke pianist), or my personal favorite wine bar, Ethos (which offers festive jello shots and the best wines by the glass). These spots are known for their warm atmospheres and festive vibes so you won’t go wrong.
What to wear to Nantucket’s Christmas Stroll
The key to enjoying Nantucket Stroll is to embrace the festive spirit through your wardrobe. On Saturday, get ready to don your most festive headgear or over the top Christmas outfit. You’ll see lots of people in ugly Christmas sweaters, plaid and sparkles but you can go as over the top or stylish as you want. Ralph Lauren vibes always fit in on this preppy-leaning island but don’t be afraid of the kitsch.
It will be chilly, we’re in New England after all, so make sure you pack layers, coats, gloves and hats in case they’re necessary!
Stroll is a magical weekend for special holiday memories. I hope you’re able to find an opportunity to experience this charming weekend and if you book your trip, let me know so I can watch out for you there!
Frequently asked questions
Q: What is the best time to visit Nantucket Stroll?
A: The first weekend in December is when Stroll happens each year - because of the tight timeframe, remember that everything will be in demand!
Q: Are there kid-friendly activities during Nantucket Stroll?
A: While I’ve anecdotally noticed this as a more adult-leaning weekend, there are absolutely festivities that are family-friendly elements, especially with Santa’s arrival. Saturday in town is going to be your top time frame but check out local Instagram accounts like @NantucketCurrent for other goings on.
Q: Do I need to book accommodations in advance?
A: Yes! It’s highly recommended to book your stay well in advance, as the weekend can get crowded and accommodations fill up quickly.
Q: What should I pack for my trip?
A: Bring festive outfits, cozy sweaters, and comfortable shoes for walking. Don’t forget your holiday headgear!
Q: Can I find local food and drink options during the event?
A: Absolutely! On Saturday in town, there will be food trucks in the market lot near Stop & Shop plus the local restaurants, coffee shops and bakeries will all be available. In the evenings there are plenty of dining options available, but be sure to make reservations early to secure your spot.
