Maine Fall Foliage at Cape Porpoise by Robert A. Dennis

“Cape Porpoise” photo: Robert A. Dennis

The coming weeks will see the beginning of the annual Maine fall foliage show, with peak colors likely arriving around Columbus Day Weekend. Kennebunkport is ready with harvest festivals, road races, trick or treating, day trips, and so much more.

Summer may be officially over – but that doesn’t mean the fun has to stop. The Kennebunks are always good for a visit, no matter the season, and fall is one of the most gorgeous times in the area. Its also an active time with lots of local harvest festivals, end-of-the-season events, and Halloween celebrations.

Just take a look and see!

Early Fall Events

Kennebunkport Conservation Trust Trail Fest – October 5th
Trail Fest is your chance to soak up some gorgeous scenery while running a 5K, 10K, or half marathon. The race ends with an all-day party including music, good food, drink, and games. All registered runners receive a Trust Trail Fest t-shirt. Learn more at

Kennebunk HarvestFest 2019 – October 12
HarvestFest is a free, family-friendly fall festival that includes a Halloween/Homecoming parade down Main Street, Farmers’ Market, Craft Fair, Book Sale, and more. Get a real taste of the Kennebunks at our annual, Maine coast village celebration. More info.

Maine Fall Foliage in the Kennebunks by Robert A. Dennis

“Adams Farm” photo: Robert A. Dennis

York HarvestFest 2019 – October 19
Enjoy live music, food vendors, a juried crafts show, games, sales, and prime Maine fall foliage. York Beach is just 30 minutes south of our Kennbunkport inn, near Nubble Lighthouse. Learn more at

OgunquitFest 2019 – October 25th-27th
It’s 3 days of fun and festivities in Ogunquit! Witer Races, River Rally, antiques, a wine tasting, costume parade, car show, and too much more to list here. Ogunquit is less than 30 minutes drive south of Captain Jefferds Inn and always worth a visit. Read more.

10th Annual Wicked 5K Road Race – October 26
Costumes are encouraged for the annual, Halloween-themed, Wicked 5k Fun Run/Walk through the streets of Kennebunkport. The race is open to all and includes amazing prize give-a-ways. Just about everyone leaves with something. Register online.

“Trick or Treat” in the Kennebunks – October 31 

Come watch as the little ghosts, pirates, and princesses trick or treat the merchants of Kennebunk and Kennebunkport. All of Summer Street will be devilishly decorated and spooky for the holiday. Lots of good, small-town fun!

Maine Fall Foliage Drives

Maine Fall Foliage in the Kennebunks by Robert A. Dennis

“Kennebunk River” photo: Robert A. Dennis

Kennebunkport is full of beautiful scenery, gorgeous architecture, and, this time of year, stunning fall foliage.

If you’re a leaf-peeper, or just someone who appreciates natural beauty, consider a stroll or good old fashioned bike ride around town, down Parson’s Way, for example. You can also hop in your car and take a tour of all the stunning Maine fall foliage in the area.

Ocean Avenue is the first drive that comes to mind. While primarily a way to see the coast – and Walker Point, the Bush compound – this drive becomes particularly spectacular come fall. Wow!

St. Anthony’s Monastery – The grounds St. Anthony’s Monastery (28 Beach Ave, Kennebunk, ME) are always good for a visit but really come to life with fall’s warm colors. Monastery grounds are open to the public year ’round, sunrise to sunset. The monastery gift shop is open 7 days a week, from March 1st to December 24th.

These are just a few, quick suggestions. For more ideas, just ask! Captain Jefferds Inn loves to share the Kennebunks and the beauty of the Maine coast with all our guests!