I’ve always wanted to go to Nantucket, so a few years ago, David surprised me for my birthday with a trip to Nantucket. We were there right before Thanksgiving and being the off season, we basically had the island to ourselves. During that trip we were told multiple times that we needed to come back for Christmas Stroll. Fast forward three Christmas’s later and David once again surprised me with another trip to Nantucket but this time during Christmas stroll and with our little boy.

I’ve always been a fan of cheesy Hallmark Christmas films and Nantucket Christmas Stroll makes you feel like you are taking a step into one of their movie sets…. The town completely transformed with Christmas decor on every store front and home, the town crier and Christmas carolers moving throughout town, adults and children dressed up in their finest holiday costumes and of course the biggest moment, Santa making his debut arriving to town by Coast Guard.

Nantucket Stroll started in 1973 when the businesses were trying to find a way to survive during the off season and have people do their holiday shopping on the island instead of escaping to the mainland. When we were there in 2022 Nantucket celebrated its 47th Christmas Stroll and being one of the first “normal” since the start of Covid, it was bigger then ever. While Nantucket is quaint and special anytime of the year the whole island really is a special place during Christmas Stroll. There is so much to see and do on this tiny island that you can make yourself as busy or as relaxed as you would like.

One tradition that is really beautiful to see is the festival of trees held at the Nantucket Whaling Museum. The Whaling museum is both beautiful and interesting. It tells 4 centuries of history about he island of Nantucket. The museum is home to many artifacts collected from the island as well as a skeleton of a large sperm whale. If you visit during Christmas Stroll you will also get to see the Festival of Trees. Over 100 businesses on Nantucket all decorate a tree for their business and they are displayed in the museum. Reserve tickets ahead of time to ensure you can get in when you would like to visit.

Nantucket also has three lighthouses to view. Brandt Point lighthouse is very close to town and also close to a nice playground to stop and have kids play. In 1746 this was the second lighthouse established in Colonel America. Since first being constructed it has been destroyed 7 times with the current lighthouse standing since 1856. It is listed on the National Register of Historic Places. Brandt Point is a great way to start your morning.

If you want to get out of the main area of town, which I recommend you do, one mode of transportation you can take is bicycle. There area couple of places to rent a bike from but we chose a place that is right off Broad Street. If the weather is nice enough riding a bike around Nantucket is very easy, safe and a fun way to really discover the island. There aren’t many ubers or taxis on the island so its also very convenient to have a bicycle as the island itself is not that big. Before renting your bicycle for your adventure stop by Island Coffee. Located on Broad Street right next to Youngs Bicycle Shop. They have been in business over 20 years and are open year round. The staff is very friendly and helpful.

Another stop out of town that is really fun and also kid friendly is Cisco Brewers. This is an amazing brewery on the island that sits on farm land. While its about a 20 minute drive, and ubers are hard to come by, they do have a free shuttle in town. It has been open since 1995 and has been called “the happiest place on Earth.” They usually have live music and it’s a fun place to visit a little ways out of town.

There are plenty of families who spend their time on Nantucket Island. That being said the restaurants are not the most kid friendly as many are higher end and very small. During Christmas Stroll most of them have a limited set menu, not only because of the amount of people on the island but also because this is their off season and after Stroll weekend many people are gone until the Tulip Festival in April. Restaurants, for the most part, are pretty high end but one restaurant that is really fun and gets into the festivities is The Club Car. It is a restaurant and beside it is a retro fitted railway car. For Christmas the restaurant, and bar especially, are highly decorated. Over the top, yes, but a fun place to go.