What do you picture when you dream of Christmas in New England? A small town square covered in snow, carolers singing in storefronts covered in holly, decorated Christmas trees on every corner? If so, you'll want to check out the Nantucket Stroll, a weekend Christmas festival held on a quaint island off the coast of Massachusetts.
The Stroll kicks off on a Friday, when boatloads of weekenders arrive from Boston and New York City, filling every hotel, bed and breakfast, and AirBnB far in advance. These festive visitors arrive in waves, filling the streets with colorful Christmas suits, hats, and costumes.
The island, which is normally very quiet in the winter, wakes up in response to all the commotion. Every shop is open and ready for peak season business. Stores give out cookies, mulled wine, and hot apple cider to entice shoppers in out of the cold.
The stroll started out as a way to bring mainlanders to Nantucket before the holidays, giving businesses one last hooray before they closed their doors for the long, slow winter. However, the event has gained quiet the following in recent years, and stores are starting to sell out of full priced items before the weekend ends!
As it grows, the weekend Christmas festival becomes more and more exclusive (and expensive), but with some planning, anyone can attend. Here are some tips to help you get to next year's Stroll like a true New Englander.
#1 Check the Date
The Nantucket Stroll is held every year during the first weekend in December. If you arrive the weekend before or after, most of the stores will be closed or only open for limited hours. The same goes for the ferries, which follow an off-season schedule this time of year except for Stroll Weekend.
#2 Plan Your Stay
Every hotel, bed and breakfast, and AirBnB will be booked for this weekend, so if you are thinking of staying over in Nantucket, you will want to reserve your room well in advance.
If you are looking for a cheaper or more last minute option, you can stay in the town of Hyannis, which is where one ferry to Nantucket leaves from. Hyannis also has a downtown you can explore on your second day. The Christmas Stroll for Hyannis is the same weekend, so there is plenty of shops and restaurants to check out Day 2 of your New England Christmas adventure!
#3 Book Your Tickets in Advance
Nantucket is an island so you need to find a way onto it! While the Stroll itself is free, getting to the island is not. You'll need to book tickets on either of the two ferry lines out of Hyannis a couple of months ahead of time to make sure they don't sell out. There are ferries over from New York City and an airport on the island as well, if that's more you style.
#4 Dress for Walking Outside
The Stroll takes place the first weekend in December every year, rain or shine, so you will need to dress appropriately. As the name implies, there is a lot of strolling during the Nantucket Stroll so you will want to wear shoes you can walk in. I usually do about 5 miles of walking on Stroll days, so comfy shoes are essential!
Next, you need to dress for the weather. December is generally cold and the Stroll is mostly an outdoor event, though you will be popping in and out of shops all day, so you will want to dress in layers. Hat, gloves, and a warm coat are key for walking around and spending time sitting outside. When indoors, you can take this warm layer off and wear something more festive.
As you walk around, you'll see groups who have fully committed to the spirit of the Stroll and dressed up as Santa and his reindeer, a group of elves, or in Christmas themed suits. So you can dress as cheery as you want and blend right in!
#5 Plan Your Breakfast
Personally, I love taking an early morning ferry to beat the crowds. From around 8 to 10 AM, Nantucket is still asleep. Not all of the stores have opened up, but you can get the best photos, and the shortest wait-times where ever you go. This is especially true when looking for breakfast places. Put you name in early and then wander around for a little while until your table opens up. By 10 o'clock, every eatery in Nantucket will have a 2 hour line, so if you are getting to the island after mid-morning, you will want to eat beforehand.
#6 Visit the Church Bazaars
Walking around town, you'll stumble upon at least 3 church bazaars. One is in a church basement and mainly sells handmade crafts and thrifted gift ideas. Another has a large outdoor stand selling hot food like hotdogs, and the steam from stall can been seen a block away. My personal favorite church bazaar is located in the second floor of a church tucked between shops. There are three rooms to the bazaar, each selling artisan jewelry, paintings, knits, and soaps. One stand sells chocolate-covered peanut butter balls that you can't miss. Buy one package for snacking as you walk and the other to bring home!
#7 Get to Cisco Early
I've mentioned the crowds a couple of times, but nowhere is more crowded during the stroll than Cisco Brewing. The line around 4 o'clock can be over 2 hours long, so you will definitely want to get here early! The first shuttles leaves from the information center around 11:30. While this might seem early, Cisco will be open and you can go directly inside to find a drink and a seat.
If you're following my early morning suggestion, spending a couple hours at Cisco in the afternoon is a great way to rest your feet and relax before visiting the last couple of spots on your list. Again, you will want to dress appropriate as most of the seating is outdoors.
#8 Eat Some Lunch
Each year, I hit 10,000 steps hours before the ferry back home, so by lunchtime, I am wicked hungry! However, so is every other stroller so the restaurants are busy. Luckily, there are a lot of options on the island!
You can grab something from the church bazaars to snack on like the chocolate covered peanut butter balls or a full lunch like a piping hot hotdog if you are looking to be quick. On the other hand, if you have a lot of time, you can put your name in at a restaurant and wait for your table to open up. This is the biggest day of the season for every business on Nantucket, so they are prepared to get groups in and out and may even have additional seating available to accommodate the large demand. Cisco has a couple of different food carts too, if you are looking to eat while you are there. I, personally, opt for eating slightly off peak time. After around 2 o'clock, the lunch rush has fizzled out so the wait times for a table are a lot shorter.
Regardless of what lunch you pick, remember that you've done a lot of walking and your body will need to refuel so be sure you and your group eat something or it will be a very long afternoon!
#9 Bring your gift list
The main reason to Stroll (other than to get in the Christmas spirit) is to shop! All of the store fronts are decorated with tinsel, evergreen, and holly, making it feel like the North Pole. Inside, there gifts for everyone on your list. There are name brand clothing stores like Ralph Laurent and Vineyard Vines, and local shops that offer something unique from vintage clothes at Current Vintage to handmade leather goods at Craftmasters of Nantucket to the latest fashions at tens of other stores.
There are a number of home stores around the island that are worth visiting, some for gifts and some just for inspiration, depending on your budget. Historically, many of these stores did sales for the Stroll, but these deals have gotten smaller in recent years as the Stroll became more popular. I still love to see the different design ideas and sometimes leave with some new home decor.
Additionally, Nantucket is a popular tourist destination, so there are a lot of tourist trap shops. Places where you can buy knickknacks that say "AUK", Nantucket sweatshirts, and little beach sayings. These are open in the winter and often have some of my favorite Stroll-themed ornaments. These stores are a lot more budget friendly and will definitely help you check a few names off your list.
#10 Do Not Miss Your Ferry Back
Most ferries are sold out weeks in advance so there are no last minute changes and with such a high demand for places to stay, there will be no open rooms anywhere on the island if you miss your boat back. Moral of the story, do not miss your ferry!
There are several ferry lines leaving from multiple docks and you will want to make a plan in advance. First, double check your ticket time and set an alarm in your phone to remind you to start walking towards the harbor. Next, double check the ferry company and which dock they leave from. Most of the time, you leave from where you were dropped off, but you will still want to make sure this is the case. Lastly, give yourself some wiggle room. I know no one wants to leave any earlier than they have to, but setting aside time at the docks in case something gets messed up could mean the difference between catching the boat and having a very cold night.