A Birthday Weekend in Nantucket

Power outages and high winds didn't stop us.

When I was signing at Mitchell’s Books with Nancy Thayer on the island of Nantucket over the summer, Nancy told me I just had to come back for Christmas Stroll. I asked what it was, and she smiled, a few patrons in the bookstore chiming in. “It’s the most special time on the island,” one woman said. “Everyone comes back for one weekend in December. The island is decorated for Christmas, and all the shops put their stuff on sale.”

I’m always up for a new adventure, and my husband and I booked our December hotel room in Nantucket a week after our summer trip.

Cue the wind. The day before we were due to leave on Friday, the Steamship Authority began cancelling the ferries due to the swells. Nantucket is thirty miles from the mainland, and the slow boat takes just over two hours. But the idea of sailing in forty-two degree water in rough conditions didn’t sound very relaxing. I texted Nancy to ask her for advice and she answered like a true islander: “If you have to take the slow boat, it’s the one I love and if it’s rocky, I like to lie down on a bench and sleep.”

When I’m nervous, the last thing I can do is sleep — but I appreciated the hearty mindset.

Luckily, the weather passed early, and our high speed ferry on Friday zipped across Nantucket Sound without problem. We felt like we were living in a Christmas fantasy as soon as my husband and I, our kids, and my mom walked up Broad Street. Historic hotels had lush garland wrapping its porches. There was a holiday wreath on nearly every door. Every several feet, there was another themed Christmas tree on the sidewalk illuminated even in daylight. Shops were selling Stroll-themed hats, scarves and sweatshirts.

We dropped our bags at our hotel and walked through town, spotting red bows tied in windows, twinkling lights lining doorways, historic whaling homes with candles in the windows, a Main Street that looked like it was lifted from a snow globe. I understood then why Nancy has written such lovely Christmas novels (Elin, too) because I had a million and one ideas for novels just people watching on Main Street.

Saturday was the official “stroll day.” “Happy strolling,” shopkeepers said when we left their stores. Other shopkeepers offered us mimosas or Baileys when we stepped inside to look around, which is an old Christmas Stroll tradition. A museum in town hosted a festival of trees. There was wreath making and historic walking tours. Tourists and locals dressed for the occasion in wild red suits with snowflake patterns or walked about as the Grinch or Santa’s reindeer. Even the dogs had Stroll scarves tied around their necks.

At some point on Saturday, an underground cable along Water Street cut power off to many stores and restaurants — some tourists had to switch hotels. Some boutiques encouraged you to use the flashlight on your iPhone to look around. Local businesses were forced to close earlier than planned, and many lost an incredible amount of money.

We barely noticed the power outages because we were waiting for Santa to arrive by Coast Guard boat down on the docks. The big guy cut across the harbor waving to the waiting crowds. After he descended from the boat, Santa walked up the cobblestones until he arrived at an antique fire truck restored by The Nantucket Hotel. My little one and I followed Santa close on his heels, Emi getting fabulous photos.

After the memorable meeting with Santa, we went and visited Nancy at Mitchell’s. She was signing books and I gave her a big hug, her eyes lighting up when she spotted me and the kids. Nancy is one of those warm individuals you feel incredibly lucky to know. “Thank you for telling me to come to Christmas Stroll,” I told her. My mom and I bought copies of her book, and she wrote a darling note inside.

While many restaurants were forced by the fire department to close due to power outages, our dinner reservation at The Tap Room wasn’t cancelled. Dinner was cozy in the tavern with a fireplace burning nearby. On Sunday, we won a lottery at our hotel to use one of their promotional cars on site (kinda brilliant) and we drove up to Sconset to show my mom the adorable houses up on the bluff. Even in winter, the ocean was the prettiest green.

When we were going home on the ferry, my little one looked at me and smiled: “I think the real Santa was on the boat yesterday.”

I had to agree; the weekend was like stepping into a scene in It’s a Wonderful Life or maybe one of those Cottage Christmas design magazines—and it all felt so magical.

“Well, everyone wants to come to Christmas Stroll,” I squeezed my little girl. “Even Santa.”

Today is my actual birthday! Woot! Tell me what you like to do on your birthday and don’t forget to “heart” this post if you like reading Dear Fiction. It helps other book lovers find this newsletter.

Have a great week, everyone! I’ll check in before the holidays next week before taking two weeks off.