Maine is always a good idea—especially in late-summer—when hydrangeas are in full bloom and lobster rolls are at their seasonal peak. Coastal Kennebunkport is a hub for both and an easy two-hour drive from Boston up Route 95. While weeklong family stays are traditionally a great way to experience its epic beaches and downtown shopping scene, during summer travel season, reservations aren’t easy to come by, and neither is fighting everyone for a classic #mainecore Instagram shot. The solution? A Kennebunkport day or overnight trip on Labor Day or in September. It will allow you to slip in and out of the best-known attractions with relative ease and maybe even score a barside seat at the hottest bites-and-bevs spots. For the ultimate K-port itinerary, we asked Jackie Greeney for her Kennebunkport must-dos—she’s co-owner and founder of Seacraft Vintage, a Dock Square mainstay containing her artfully curated collection of Maine maritime finds. Here’s a list of the best things to do in Kennebunkport if you’re traveling on Labor Day or beyond.
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Best Places to Stay in Kennebunkport
While most hotels are booked well in advance of the summer season, Kennebunkport has everything from seaside cottages for rent by the week to prestigious “grand dame” hotels overlooking the ocean and everything in between. Our favorite place to stay is The Lodge on the Cove—31 newly renovated queen, king and bunk-bed rooms designed to harken back to a 1960s-style drive-in motor lodge. There’s a pool, gameroom, movie nights and even s’mores kits for nighttime campfire chats. Keep your car parked there and then make the relaxing 20-minute walk to Dock Square past some of the prettiest harbor views you’ll see. Greeney is a fan of the KRC properties, too. “The Yachtsman is a really good spot for the over-50 crowd… Every single room is ground level with a terrace three feet from the water. It’s very quintessentially Maine, and they do allow dogs.” For something more special and romantic, “The Colony is historic, with a pool that looks out over the ocean—it feels very Dirty Dancing-era old-school Maine.”
Best Brunch Spots and Coffee Shops
There is nothing better than a locally made baked good, and Kennebunkport has loads to choose from—even a highly decorated chef. Bev’s Café and Market is owned by the former Zuni Café executive chef and his pastry chef wife. “One of the places we really love… is Beverly’s. Their breakfast specials change daily—like a French onion soup open-face omelet with Gruyère and croutons. It’s just absolutely amazing,” says Greeney. Around the corner, Boulangerie boasts some of the best croissants, muffins and quiche around (and don’t forget to pick up a homemade dog biscuit or two.) And think you can’t get a great bagel in Maine? Think again. “K-Port Bagels is really good, too…” says Greeney, “The owner learned the art of bagel making in New Jersey and their jalapeno bagels are so good. They just started doing breakfast sandwiches this year, and even though I lived in New York for 10 years, I think they’re just as good.”
Late-Summer Activities (No Reservations Required)
While Dock Square, Goose Rocks Beach and Walker’s Point Estate (the Bush family compound) are big draws, Greeney says there’s a quieter part of Kennebunkport that’s often overlooked. “Cape Porpoise is quintessential Maine—fish houses on stilts, lobster boats, the lighthouse. People stay in Kennebunkport for a week and still miss it, but it’s the heart of the area.” Open at 5 p.m. daily, Nunen’s Lobster Hut is famous for hot boiled lobster and homemade pie, and you don’t need a reservation (but you will need cash.) “They’ve been lobstering for over 100 years. Two lobsters for about $30. It’s the most delicious lobster anywhere.” Drive up to Pier Road for Goat Island Lighthouse views and try Casa Seventy SevenSeafood Shack & Bar for oysters and cocktails or Ultramar for grilled seafood done Mediterranean-style, both by the same team from The Lost Fire, a restaurant and outdoor fire pit devoted to Patagonian cooking that’s become one of the most popular in the area. Both are walk-in friendly with ample terrace spots for the best harbor views. If you’re considering a trip in August…just wait.“September is without a doubt the best time to come… The ocean’s warmer, the crowds are gone, and all the seasonal restaurants are still open.”
Antiquing and Gallery-Hopping
When asked about her favorite places to shop in Kennebunkport, Greeney lights up. There are almost too many to choose from, but in narrowing it down, she starts with Snug Harbor Farm, a garden center, duck farm and gift shop that’s like a secret garden all of its own. There you can find everything from pocket guides to coastal Maine to artisanal Neem oil to locally made ceramics. Across the street, Bulfinch Antiques has stunning coral finds, coastal art and beautiful rugs. On Port Road, there are loads of galleries to choose from, but KW Contemporary Art by gallerist Kiersten Wilcox is a standout. “It always has something fresh—she does such a good job keeping the gallery scene vibrant.”
Peaceful Walks and Waterfront Views
Coastal Maine has been drawing crowds for centuries thanks to its untouched craggy coastline and stunning seaside views. There’s so much to explore, but Greeney’s distilled her nature lover’s starter pack for first visits-they’re especially peaceful this time of year. “The Rachel Carson Preserve is a nice marshy loop along the waterfront—easy with a stroller, and just a peaceful walk,” she says. For families, there are three main beaches in Kennebunkport, plus a few close-by. “Mother’s Beach just rebuilt its playground right on the sand… it looks like a lobster shack and lighthouse kids can climb into. It’s a really cool spot.”
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Where to Dine in Town Without Stressing About Reservations
In high-season, good luck. Kennebunkport hotspots book up weeks, if not months in advance. However, there are some spots that take walk-ins, and early bird diners will have luck too. “Our favorite spot for dinner is Wandby Landing. It’s Italian-inspired with homemade pastas, cozy fireplaces in the off-season, and really great service,” shares Greeney. In September, you may have more luck getting a table at townie-favorite Chez Rosa.“It’s run by a local couple… their French fries are unbelievable, and they also do fondue. We love it in the cooler months.”
The Best Shopping & Souvenirs
And don’t miss Greeney’s own store. “Seacraft Vintage is all about mixing vintage finds with unique coastal-inspired goods. We partner with artists so you’ll find things you won’t see in every other Kennebunk shop. For example, the carved fishermen we carry were popular souvenirs in the ’60s and ’70s—people still love them now.” You can visit the original tiny shop at The Shops at Morning Walk in lower village, or explore the new larger Dock Square location. While you’re perusing the Shops, don’t forget to stop into Good Stock Charm Bar. “Goodstock’s charm bar went viral last summer. You can make your own charm bracelet or necklace—it’s become a multigenerational thing for moms, grandmas and granddaughters.”
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Scenic Views You Can’t Miss
A sailboat docking in the marina of Kennebunk River with flowers in foreground
Finally, no trip to Kennebunkport would be complete without setting sail—if you can.“In town there’s also the Schooner Eleanor, which is a really beautiful sailboat you can take out for a sunset sail or daytime sail.” And for a truly local experience, stop into Kennebunkport Farmer’s Market on Saturdays, rain or shine from May to November, featuring all-Maine producers. “The Kennebunk Farmer’s Market is amazing—it usually has someone singing, things for kids, and it runs well into the fall, even up to Thanksgiving.”
Related: What It’s Really Like to Stay at the Chicest Hotel on Nantucket
Sources:
Jackie Greeney, co-owner of Seacraft Vintage along with her husband, Paul Havel.
