5 Reasons to Visit the Kennebunks This Fall/Winter

5 Reasons to Visit the Kennebunks This Fall/Winter

Escape the bustle of summer in Maine and soak up the small town, local charm in crisp fall air.

You can't resist the fall colours of Kennebunk, Maine. All photos by Natalie Taylor.

You can’t resist the fall colours of Kennebunkport, Maine. All photos by Natalie Taylor.

It’s hard not to associate summer with the state of Maine. You can already picture wearing your favourite striped shirt with a pair of khaki shorts, eating a steaming lobster roll on a sailboat. That said, as much as we love summer in the state of Maine, we’ve realized what a perfect escape it is in the fall. When we went to Kennebunkport, Maine (also affectionately known as The Kennebunks), a seaside town, 40 minutes away from Portland, Maine, we fell in love with it immediately, if not because it was an excuse to still wear our striped shirts with a cozy blanket scarf over it and break out the wooly socks pulled up over our jeans. Here are five more reasons to visit this special place in the cooler months.


1. No Crowds
The Kennebunks is chock full of tourists in the summer season but when you’re traveling from October to December, you’ll practically have the place to yourself not to mention better rates at swank hotels like The Boathouse Waterfront Hotel, The White Barn Inn, and cozy cottages like Hidden Pond and Captain Jefferds Inn. Sailing tours like the Pineapple Ketch will operate in the autumn season if the weather cooperates giving you a chance to get a private tour when the fall colours are in peak season.

2. Fall Colours
The jewelled tones of the trees adds another depth of character to the small town charm of the Kennebunks. Check out Highway One and Ocean Drive along the way to Cape Porpoise (make sure to grab a dark and stormy to embrace the dip in temperature at local watering hole, The Ramp.) Hiking trails are plenty in the area  and the best spot to shuffle through those leaves is at The Wells Reserve at Laudholm. Walks of all ages and athletic types can stroll the trails. Don’t forget your best plaid ensemble for a photo snap (and feel free to follow us on Instagram @travelstylemag!). The reward is the ocean view at Laudholm Beach at the end of the trail, showcasing that the destination is just as worthy as the journey.


3. Get Spooked
Halloween is a big deal in the Kennebunks and it’s a fun way to travel in the off-season. Hop aboard the Spirit of Massachusetts in the downtown harbour for their annual Ghost Ship Party. Locals are decked out in their costumes, drinks and hors d’oeurves are aplenty, and the night is not complete without dancing to MJ’s “Thriller,” on deck. On Halloween night, Summer Street is closed off to over 1,000 kids waiting to get their trick or treat. The houses are decorated to spook, including a haunted barn. Not in town, during Halloween? Take a haunted walk with Captain Moody who will regale you with haunted tales surrounding iconic spots in town and include a stop to a seance society.

4. Festival Season
Halloween is just the start of the many festivals that light up the town of Kennebunkport. In late November, Pyjama Shopping Day is an initiative to shop local and in return, receive 40% off your purchases. It’s an excuse to stay downtown to witness the tree lighting ceremony to kick off the holiday season. During the first two weeks of December, the Christmas Prelude is the reason to visit the Kennebunks and meet locals. You can’t miss signature events such as the Lobster Trap Tree Ceremony Lighting, holiday hat and pooch parades; and of course, Santa’s arrivals both by lobster boat and fire engine. This is the perfect time to experience the Kennebunks and enjoy quality time with the family.


5. Romantic Moments
Whether you’re taking a drive through a canopy of orange and red tinged trees; indulging in lingering meal at Ocean Restaurant with a view of Walker’s Point (the summer home and compound of President George Bush); or taking a sleigh ride for two at Rockin’ Horse stables, the small town charm of the Kennebunks makes it easy to get swept up in romance with your sweetheart. In February, Paint the Town Red is a month-long event that celebrates couples with various romance packages at various accommodations and features special events like a bubbles and a truffle making class. The highlight of the month is the Frosted! Party, showcased by an ice bar, snacks and s’mores (any party is made better by s’mores). You can even win a trip for two to the Kennebunks!

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This trip was generously sponsored by the Chamber of Commerce of Go Kennbunks