For many, summertime means heading up to the Maine coast to explore the many quaint seaside villages that extend from the New Hampshire border all the way up to Bar Harbor and beyond.
And one of the most popular towns is Kennebunkport, a charming old spot that typically sees its fair share of tourists when the weather is warm. After Labor Day, however, things tend to quiet down a bit and once the fall comes around, it can feel like you have the whole place to yourself even though many businesses are still open.
To some, autumn and early winter are the best times of year to come here (especially if the weather cooperates), and Kennebunkport has quite a different feel to it as the leaves start to turn and the smell of woodsmoke starts to drift through the air. And while some of the better-known restaurants are closed until the spring, there are still a number of great dining spots to hit in and around town, including some that have a real local flavor to them.
Kennebunkport is, to some, all about its picturesque village center, where you can walk from shop to shop, relax by the waterfront and stroll along its narrow side streets. But there’s much more to the town than just the downtown area, some of which, by the way, is not actually part of Kennebunkport (more about that in a minute).
Just south of the center along Ocean Avenue is Cape Arundel, a toney area that attracts artists and photographers and has stunning views of the ocean, including from Walker's Point, a tiny peninsula that includes the Bush family compound.
Ocean Avenue soon becomes Shore Road and eventually leads into Cape Porpoise, an old fishing village within Kennebunkport that wouldn’t be out of place in Downeast Maine and which has mesmerizing views from a dead-end road that branches off Route 9 in the village center. Route 9 (which is the inland route from Kennebunkport Village, by the way) heads northeast from Cape Porpoise and soon skirts Goose Rocks Beach, another village within the town that has a general store, a large hotel, and one of the most gorgeous beaches in Maine if not all of New England.
Much of the rest of Kennebunkport is made up of deep woods and unspoiled farmland and is well worth exploring — especially by bike, when the weather is nice — and back to the town center for a second. The part of Kennebunkport village on the west side of the river? That’s actually part of the neighboring town of Kennebunk and is called Lower Village (and is every bit as postcard-perfect as Kennebunkport Village).
As mentioned earlier, some of the restaurants in and around Kennebunkport are seasonal and are either closed or about to close. But a number of options both in town and nearby remain open until the end of the year—and in some cases all winter long.
Right in the village center is a decades-old, family-friendly restaurant called Alisson's, which currently has indoor and outdoor dining and takeout/pickup. It features classic Maine seafood dishes such as lobster rolls, steamed lobster, fried clams and mussels while also offering items such as pizza, wings and poutine to those who might not be in the mood for seafood.
Just across the river in Lower Village is Federal Jack’s, a second-floor brewpub and comfort food spot with jaw-dropping views of the water, and which features some tasty Shipyard beers. (Shipyard actually started out right here as Kennebunkport Brewing Co.)
A real local hangout can be found a few miles away on the aforementioned Bickford Island in Cape Porpoise, and The Ramp is something else — a watering hole with unforgettable harbor views and a place where you’ll see a mix of local fishermen, wealthy Kennebunkport residents and the occasional tourist who may have gotten lost, and this is a beer and a shot type of place that also happens to have some great food, including excellent takes on clam chowder, burgers, tacos and crab melts.
If you’d like to take a bit of a road trip for food, several good options await, including a restaurant, bar and brewery in an old mill building a short ride north on the Saco-Biddeford line called The Run of the Mill. This place is actually located on an island in the middle of the Saco River and features a mix of classic and New American fare. The space is massive, with lots of seating in its rustic indoor area and a large outdoor patio overlooking the water is used when the weather cooperates.
Heading south from Kennebunkport on Route 1 in Wells is Congdon’s, a roadside breakfast place that lures people from miles away (including Boston!) for its marvelous doughnuts. Congdon’s also has other breakfast items as well including waffles, French toast and pancakes, but keep in mind that it is only open for takeout for the time being.
A bit further down Route 1 in Ogunquit is the Ogunquit Lobster Pound, an old-school spot under some massive pine trees that's a favorite among locals for its no-frills atmosphere and its outstanding boiled lobster, lobster pie, lobster stew dinner, lobster tail dinner and so much more. (Keep in mind that this place is seasonal and is currently open only Friday through Sunday for now.)
Shopping in Kennebunkport can be fun if you’re a food/drink lover, and you can certainly find some high-quality Maine products here. Maine-ly Drizzle is a friendly second-floor spot right in the heart of Dock Square that features an endless array of olive oils and balsamic vinegars, and the big danger here is that everything can be sampled, so it is best to pick and choose what you really might want to try before buying anything.
For those with a sweet tooth, The Candy Man in Dock Square is a must, as they make all kinds of delicious items from scratch, such as fudge, salt water taffy, chocolate turtles and peppermint bark. Heading over the river into Kennebunk’s Lower Village is an old-fashioned general store called H.B. Provisions, and here you will find everything from sandwiches to coffee to regional items such as blueberry hot sauce. If you’re a beer drinker, you’ll also find some local brews as well.
Much of the fun of Kennebunkport in the off-season is simply taking walks to check out the fall foliage in October, the holiday lights in late November and December, and the wild and wooly ocean at any time.
One of the simplest and most enjoyable ways to stretch your legs is to walk around either side of the Kennebunk River between Lower Village and Kennebunkport Village, especially around the time of the Christmas Prelude in early December when the town takes on the look of a Norman Rockwell painting. Another good walking area is the Kennebunkport Historic District, much of which lies roughly between Ocean Avenue and Maine Street just south of the village center, and which is where you’ll find the types of old homes that you can generally only find on the New England coast.
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Kennebunk Beach, which is a short distance south of Lower Village, is a great place to saunter around, and the lighting this time of year — especially later in the day — can be almost surreal, as the setting sun starts to work its magic on the sand and the water. Cape Porpoise is another spot just made for walking, be it the laid-back village center (which, in classic Maine style, sets up a Christmas tree made up of lobster traps around the holidays) or the very tip of Bickford Island. There you can catch a glimpse of the working harbor from a rise by the end of the road or down at the docks, which is a perfect place to catch a sunset.
Finally, Goose Rocks Beach in the offseason is absolutely heavenly, and you may be the only ones there depending on how late in the season you decide to go.
There’s a reason why the rich and famous have been spending their summers in Kennebunkport for decades, but it’s not just a town for wealthy folks and celebrities — and once the weather starts to turn cooler, you’ll find that it becomes a low-key town full of locals who live here for its scenic beauty and its great quality of life.
While the restaurant scene may not be quite as booming as it would be in July or August, the food options that remain this time of year include some really good ones, and chances are you might get to see some real local flavor as you dine there.
