A happy couple drinks coffee outside at a Christmas market.
These Holiday Dates In Kennebunkport Include A Cookie Crawl, Wine, & Pups


Have you ever watched a holiday rom-com and wondered if a festive town that hosted a bunch of unique holiday events like that actually exists? Well, Kennebunkport, Maine is that dreamy destination, and it can be the backdrop to your very own romantic holiday movie with your significant other if you're looking for a getaway. When you're planning your trip, consider these holiday date ideas in Kennebunkport in December 2019.

Kennebunkport is a charming coastal town that's great all year-round, but it's especially dreamy around the holidays. For the 38th year, Kennebunkport has put together their Christmas Prelude celebration that takes place from Dec. 5 to Dec. 15, 2019. If you live in the New England area, it's easy to take a train ride to Kennebunkport for a romantic getaway with your partner. All you need is the right itinerary — and they have you covered with the most festive one of your dreams.

Don't forget to snap some adorable selfies for the 'Gram while you are checking out the holiday decor, enjoying the Christmas tree lighting, or going on a delicious cookie crawl with your love. After all, this town is a perfect destination to start a new holiday tradition together.

The Tree Lighting Ceremony Will Light Up Your Getaway

The tree lighting is the start to every holiday season. Once the decorations have been put up, it's time to get into the full Christmas spirit.

Kennebunkport's Tree Lighting Ceremony will take place this year on Dec. 6, 2019 in Dock Square. Cuddle close with your bae (and some hot cocoa) while you watch the ceremony, and take some cute selfies together in front of the beautiful lights.

Every Christmas Should Start With A Cookie Crawl

Santa would agree that it wouldn't be Christmas without some cookies. If you and bae are foodies, you might want to go on the Prelude Cookie Crawl. On the crawl, you'll visit shops and Inns to sample their very best holiday cookies, and then decide on which one is your favorite.

This sweet crawl is happening Dec. 9 through Dec. 12, 2019, and tickets are only $10 per person. Once you choose your fave cookie, you can go back and purchase a bunch for your friends and family to try too.

A Maine Wine And Chocolate Pairing Is The Ultimate Couple (Besides You And Bae, Of Course)

Just like you and bae pair so nicely together, so do wine and chocolate. If you're both 21 or up, stop by Sweetgrass Winery in Kennebunkport for a pairing of Maine wine and chocolate.

On Dec. 12, 2019, chocolatier Dean's Sweets will be doing a holiday tasting at Sweetgrass for only $6 per person. Who knows, you may find a match made in heaven and know exactly what to bring to your family over the holidays.

A Holiday Wine And Bubbles Event Is Not To Be Missed

If you need a little more bubbly in your life, you and your SO can attend the Holiday Wine & Bubbles event at The Boathouse Waterfront Hotel in Kennebunkport. According to the Eventbrite description, you'll learn what wines pair nicely with different holiday entrees, and how to choose the proper dessert wine too.

On top of that, you'll walk away knowing the best bottle of bubbles to bring to the holiday parties you're invited to. Each ticket includes four tasting pours, and is only $20 per person. Plus, it all takes place in the gorgeous Boathouse Waterfront Hotel, which is the epitome of romance.

This Pooch Parade Is Sure To Make You Smile

The Annual Pooch Parade is happening again for the 9th year in Kennebunkport, and if you love dogs — especially dogs in holiday attire — you won't want to miss this. You can either watch or take part in the parade with your furry friend. Just think of how much fun it would be for you, bae, and your pup to wear matching holiday sweaters.

'Tis The Season For A Jazz Christmas Brunch

As part of the Christmas Prelude celebration, Kennebunkport is having a Jazz Christmas Brunch at the Kennebunkport Inn on Dec. 15, 2019. Brunch is always a good idea, and you can't pass up on the opportunity to savor tasty food while listening to jazzy Christmas music.