Kennebunkport, Maine, is probably best known as the summer home of the Bush family. It is a fishing village on the southern shore of Maine. In the summer it is a very busy place with tourists and beach goers. At Christmastime it is a busy place again as Kennebunkport hosts Christmas Prelude, a two-week-long Christmas festival. The festival is widely attended, and Kennebunkport has been voted the number two Christmas town in the the United States by HGTV!

I have had this on my Christmas to do list for nearly a decade, but work pressures, kids school events, and general life have kept me from it. This year we were finally able to go!  The list of things to do is massive, so we each chose what looked like the most fun and spent the weekend checking them off our to do list.

Best Things to do in Kennebunkport at Christmas

Prelude Trolley Ride

The trolley museum in nearby Arundel features trolley cars from around the world. They have been lovingly restored by volunteers who obviously have great love for these relics from the past.

During Christmas Prelude the trolley museum offers $10 rides on a decorated trolley. Our ride included free hot chocolate and homemade cookies. We enjoyed learning the history of trolleys while we lumbered along on a rail laid for the museum. The Christmas wreaths flopped rhythmically in time with the engine, and we passed a very pleasant 20 minutes. My youngest especially enjoyed the ride as he has always been a train enthusiast.

Plan on 1 hour

Christmas Hat Parade

The annual Christmas hat parade takes place in the center of town and features handmade Christmas hats of all varieties. The designs run the gamut from fairly basic Santa hats to lobster trap hats. Our favorites were the out-of-the-box type of hats. The parade starts at Dock Square and anyone can join in the fun. Just get there early enough in order to enter the parade yourself.

In preparation for the parade we made some Christmas hats of our own! We noticed fun hats on lots of other spectators as well.

Plan on 1 hour

Candlelight caroling at the Fransciscan Monastery

The grounds of St. Anthony’s Monastery is awash with candlelight during caroling. Traditional Christmas songs are interspersed with the telling of the story of the birth of Christ. Candles are handed out at the entrance to the field along with the words to well-known carols. This sing along is a special event in Christmas Prelude suitable for all ages.

Tips:

• The caroling lasts for about 45 minutes, so your little ones should be able to last! Plus there is lots of room on the edge of the crowd for running around.
• Dress warmly as the caroling takes place outside.
• There is no parking at the monastery, but it is about a 10-15 minute walk from the center of Kennebunkport. Plan on parking and walking.

Crafts at Christmas Prelude in Kennebunkport

Different businesses offer crafts for kids of all ages! We saw ornament decorating, wreath making, hand painted signs, cookie decorating, and more. If you are there for the entire weekend you can check out most of the crafts, but you will have to choose if you are there for only a day!

Craft fair

There are multiple craft fairs scattered around Kennebunkport. They are great places to step into to warm up and do some Christmas shopping. You will find a lot of variety from fair to fair, and prices seemed to be very reasonable.

Window Shopping

The entire town of Kennebunkport puts on its Christmas finery for Christmas Prelude. You could spend hours shopping or browsing in all the shops near Dock Square. Every store has twinkling lights and Christmas trees, and many were offering candy canes or hot chocolate.

Santa comes to town on a lobster boat

This was one we were all looking forward to, but torrential rain put a damper on events throughout the festival. We ended up leaving town after we found that the boat rides were closed, the caroling canceled, and s’mores and Santa was canceled. We will have to come back next year to see the jolly guy!

Tips:

• Parking is very difficult! There seems to be more demand than space in this small seaside town. Once you find parking, stay there for the day. Most things are walkable so you shouldn’t need to move your car. However, things like the trolley ride are in nearby towns. Do those first and then head to Kennebunkport.
• Many events only took cash.
• Strollers are great for Kennbunkport. Everything is paved and stroller friendly.

Are you looking for more New England Christmas events? Click here and here!

Like this article? Pin it for later!