We Bought a Farmhouse

stories of renovation, home decor inspiration & sprinkles of country life

Powered by Blogger.

The Nantucket Christmas Stroll

This was the trip that almost didn't happen! We booked our inn months ago, and in the chaos of trying to finish our guest room and clean up the house for the holidays, we just kept putting off booking ferry tickets for our excursion to Nantucket for the Christmas Stroll. When we visit Nantucket in the summer, we usually book our ferry 1-2 days prior because want to go on a day with nice weather, so that was also always in the back of our minds. Oh, we have time, we kept saying.

So then, about 9 days before our trip, we finally dedicated time to book our ferry ride, and I kid you not, every ferry was sold out.

We couldn't believe it.

We called all the ferry lines, asked if they had any suggestions. We looked at other ways to get on the island (flights were insanely expensive, not even sure why we looked into it). And finally, after two days of having no luck, we just decided we'd go to the Cape and make the best of everything it had to offer since our inn was non-refundable at this point. The ferry lines told us that sometimes people cancel, and to just keep checking the site, but I was pretty convinced Nantucket wasn't meant to be this year. Sometimes, a ferry out to the island would become available, but no ferry back, and we couldn't risk being on standby and getting stranded on the island (especially because it's pretty expensive).

Then, a few days before leaving, Josh was stalking the Hyline website, and someone cancelled their ticket. He booked us for the 9 a.m. ferry out, and we were able to get a ferry back at 4:40. And so, we were back on track.

We arrived at the Hyline terminal in Hyannis an hour before our ferry departed because we were that excited. We were the second people in line to board, and Josh thought I was crazy for jumping in line in the freezing cold when there was a perfectly good (and warm) sitting area in the terminal. We waited in the line, outside, for 40 minutes, and I was glad I did because the ferry was packed and the line to board got pretty long. We had our pick of any seats on the ferry, so it paid off.

We didn't really know what to expect for this excursion. I tried to do a lot of research, but it didn't really amount to much. The Nantucket Christmas Stroll has a website, which lists all the fairs and activities for each day, and it was a little helpful, but in the end, we really had no idea what we were doing. So we made our own itinerary.

As soon as we got off the ferry, we headed to Brant Point Lighthouse. I really wanted to see the big wreath they put on the lighthouse, and was determined to get a picture of us in front of it. I love Brant Point - it's the first thing you can see on the island when your ferry approaches, and the last thing you see as your ferry departs for the mainland. And it just makes me so happy.

On our way to the lighthouse, though, we crossed a bridge to see the little boat with the Christmas tree inside. This little boat is kind of famous to those familiar with the island - paintings of it were sold around the town when we were there, and it's photographed a ton. I don't really know the story behind it, or if there's even a story or who owns it, but it was on my list of things to see. And guys, it was pretty darn cute. Everyone that walked by stopped to see it, and everyone was smiling. It's such a small little thing, but it seemed to brighten so many people's day, including mine.

After the lighthouse, we meandered back toward town so we could visit the Whaling Museum. For the Stroll, they decorate tons of trees to display in the museum, and you also have access to the exhibits inside, which we had never visited. It was $20 per person, but it was well worth it. All the trees were decorated by community members and local business, and they were so heartwarming to take in. I took photos of some of my favorite trees, and posted them below. The museum itself was also really entertaining and interesting. It even had a rooftop observation area with a great view of the island, and we had never even known that it was there.

Inside the Whaling Museum.
Display inside the Whaling Museum.

View from the top of the Whaling Museum building.

The rest of the day, we just kind of went wherever we felt like it. We didn't make any lunch reservations because we weren't sure what restaurants would be open for the Stroll, and we were glad we didn't because we ended up snacking from food vendors all day. Right at the wharf when you exit the ferry, they had food tents which were run by the community, and usually benefited a school or an organization. They offered clam chowder, chili, home-baked goodies, hot cocoa, popcorn, etc. I got chowder, a few cookies and a hot cocoa. We also stopped by a bakery and Josh got squash soup and I got a gingerbread cookie. One of the sandwich places we like, Fresh, was open just for the Stroll with a special menu of comfort food. We got a grilled cheese, and it was seriously one of the most amazing grilled cheeses we've ever had. We split it, and we kind of wished we had gotten our own because it was that good. And then finally, I stumbled across an oyster vendor down by the wharf off to the side, and got some amazingly fresh oysters for $5. I'm honestly still thinking about them.

Seeing the town decked out for Christmas was just so amazing. All the main streets in town were lined with Christmas trees, and each storefront decorated them with a theme. The main road was blocked off to cars, so you could wander in the street to take it all in. All the stores re-opened for the weekend, and most of them put a lot of care into their window displays, which were so fun to walk by and take in. There were only a few stores that didn't seem to really put a lot of effort into their Stroll displays, and you could tell they literally just opened their doors for the weekend because they barely had anything, and it was picked over from the summer season. A lot of stores were also doing sales to clear inventory before they officially closed for the winter.

This whole street was blocked off to cars, so we were able to walk in it whenever we wanted.

One of my favorite store-front trees.

I was all googley-eyed over these dished at the Lion's Paw homewares store.

I loved the clamshells strung through the cedar garland on this table in Nantucket Looms.

One of the big events is the arrival of Santa on the island. As two, child-free adults, this wasn't exactly top of our priority list, so we weren't planning on seeing it. But, we just so happened to be coming out of a store when he was driving down the road, so I was able to grab a quick picture. It was actually kind of cute.

A lot of stores were serving drinks, many with alcohol mixed in, too! One store in particular was offering traditional Swedish Glogg, and Josh was pretty excited about it. It was really tasty, I will admit.

My general thoughts and observations from the day
Guys, this was really fun. I don't think it's something we'll do every year because for us, it's a little bit of a hike to get there and we really have to make it an entire weekend trip. But every now and then for a festive getaway, it was really, really delightful. I would definitely recommend it if you have the time and are looking for a Christmasy destination.

The weather really helped. It was sunny and mid-40s the whole afternoon, and there was barely any wind. I imagine that if it had rained, it would definitely make the day a little less enjoyable. The only thing that could have made it better is if it snowed.

One thing that surprised me was how crowded it was. In the summers during peak season, it's never been as crowded as it was during the Stroll. Granted, it was a one-weekend event, and we were there on Saturday, but I wasn't expecting the crowds we experienced. The ferries were full without any empty seats, and there were times we couldn't even walk into some of the stores because they were so packed. Our innkeeper warned us that the Stroll had become really popular over the years and that it draws quite the crowd, so we were prepared for it ahead of time, and it didn't ruin our time there.

If you're going for the day, you don't really need a reservation if you like to graze on food from vendors. We were sufficiently full the whole day, and we literally just snacked from different places, sampling things as we strolled along. It was perfect. Many of the restaurants looked full with crowds waiting outside, so if you want to eat at a restaurant for lunch or dinner, I would recommend making reservations ahead of time.

The Stroll offers quite a few craft fairs throughout the weekend. We attended a few, and found them to be lovely. The book fair was actually kind of sad (in the basement of a building with a few tables of books). The craft fairs had some really nice vendors, but just not anything we were shopping for, unfortunately. We didn't end up getting anything from the craft fairs, but many of them were located right in town, and I would recommend taking a peek.

If we had more time, we would have wanted to venture out to Cisco Brewery. They had shuttles going there from town, and it would have been easy to do. But since we had to head to our ferry by 4:15 to make sure we got a seat together, we were short on time. But just know that if this is something you wanted to do, you can definitely get there without having a car on the island.

Budget time to just wander. Part of the fun for us was just wandering the streets and seeing all the decorations. It was nice to escape the crowds every now and then and venture to the side streets and see the houses glowing with lights, and seeing the perfectly decorated window boxes and seaside-themed wreaths.


  1. How beautiful...we went to a little town near us that was supposed to be Whoville for Christmas but many of the merchants had not gotten the memo apparently as we were disappointed by our trip there. We do try to do some Christmasy trips this time of the year and it is always fun.

    1. Awww, what a bummer! Hopefully you can at least laugh about it now! :)

  2. Oh my goodness, I'd like to go at least once just to see the wreath on the lighthouse, and the tree in the wee boat! It all looks pretty darn magical.

    I wouldn't want to brave the crowds on a yearly basis, but I agree that it'd make a festive weekend!

    And that whale skeleton is surprisingly elegant.

    1. The lighthouse wreath was pretty epic! Definitely not every year, but even if we only ever go just the one time, I'm so happy we have the memories.

  3. You took alot of pictures. Feels like I'm there...your hair has gotten SO LONG! Looks pretty!

    1. Ha! I know, I took wayyyyyy too many photos. Everything was so picturesque I couldn't help myself. And I know! My hair is only this long because I'm lazy and haven't gotten to my hair stylist since like June. Oops!