24 Romantic Things to Do in Kennebunkport in Winter

Kennebunkport Maine sleigh ride

  1. Cuddle beneath the blankets as a draft horse pulls your carriage through a fresh fall of snow on sleigh ride for two at Rockin’ Horse Stables. Finish with a hot chocolate finale.
  2. Head to Cottage Breeze Day Spa for a couple’s massage or spa treatment. You’ll leave relaxed & rejuvenated.
  3. Get outside and walk the Ocean Avenue loop from in-town to Walker’s Point (Approx 4 mi. round-trip). Along the way, you’ll see stunning vistas of the ocean, Saint Ann’s, historic summer homes, Spouting Rock and Blowing Cave, before reaching the Bush Compound.
  4. Head to The Burleigh at the Kennebunkport Inn for dinner on Friday night, and stay to enjoy live entertainment..
  5. Take your best canine pal for a walk on Gooch’s beach. Cap off the walk with a treat for your furry friend at Scalawags.
  6. Pop into Mornings in Paris cafe for unique pastries and house-brewed coffees served with a side of Parisian ambience.
  7. Design a custom piece of jewelry at Coastal Jewelers.  Choose from select gems or Maine’s prized watermelon tourmaline.
  8. Spend an afternoon admiring local art & meet the artists at Maine Art Gallery, R. Paine Gallery, F-8 Gallery and Minka.
  9. Dance the night away at Pedro’s to the music of local Latin-inspired bands. Sample over 10 different varieties of premium tequilas in custom housemade cocktails.
  10. Attend a  cocktail class at the Kennebunkport Inn. The skills and knowledge you will pick up can be used year-round to impress your friends.
  11. Take a Brewery tour at the Shipyard at Federal Jack’s — Maine’s largest craft brewing company.
  12. Head to Cape Porpoise for lunch at The Ramp. The cocktails are classic, the pub fare is expertly crafted & the views of the Goat Island Lighthouse are iconic.
  13. Bring your x-country skis & explore the trails of the Smith Preserve, known to locals as the Town Forest.
  14. Shop for the hip, trendy & expertly crafted wares in Dock Square.  Daytrip Society, Minka, and Julia’s Gifts are a few of our favorite shops.
  15. Walk the length of Kennebunk & Gooch’s beach. If you’re steady-footed, climb the jetty & stand where thousands of couple’s have made their wedding engagement.
  16. Sign up for a cooking class at Ocean.
  17. Attend a book or poetry reading at the Graves Memorial Library.  Listen to stories from local writers & shop the book sale.
  18. Dine at the White Barn Inn: Maine’s only AAA 5-Diamond award winning restaurant. The meal, setting & service are impeccable.
  19. Show off your singing talents at Alisson’s Karaoke nights.  Remind yourself (and your love) of your sense of humor & disco falsetto.
  20. Stroll on Goose Rocks Beach & take in views of Timber Island. The beach is pristine & was the main access point for residents to off-load livestock in the 1700s.
  21. Have breakfast with locals at the Musette in Cape Porpoise. Kicked-up classics like the Daily Scrambler & housemade corned beef hash make this spot a favorite.
  22. Bring your ice skates and head to the Waterhouse Pavillon in downtown Kennebunk. This newly built arena has perfectly groomed ice.
  23. Take in the historical buildings that line the streets in Kennebunkport and neighboring Kennebunk, made even prettier in winter with by fluff of snow powdering their edges.
  24. Grab your snowshoes and head south of town to the Laudholm Farm. The nature preserve on the the water is a great place to catch the wintry landscape of the forest & ocean.