1. Where to Stay
Have breakfast delivered to your doorstep at Hidden Pond (from $399, including activities), a 60-acre wooded retreat where 35 spacious bungalows and cottages are nestled among birch trees and equipped with indoor-outdoor showers and Frette linens. Spend an afternoon hiking, taking a watercolor class, or picking blueberries from the garden before heading to dinner at the popular farm-to-table restaurant Earth and making your own s’mores at the nightly bonfire.
Cozy up in the Cottages at Cabot Cove (from $199, including breakfast), where sixteen small, wooden houses sit in a semicircle beside a tidal cove fed by the Kennebunk River. The style varies by cottage—from contemporary, neutral palettes to bright floral patterns— but full kitchens and private patios are standard features. Grab a rowboat or kayak at the dock if you want to fish, or bike to downtown Kennebunkport on one of the provided beach cruisers.
Awake to the sounds of the ocean at the Beach House Inn (from $109, including breakfast), a 34-room property set between Mothers Beach and Gooch’s Beach, both known for their prime surf. The rooms aren’t as large or plush as those at better-known sister property the White Barn Inn, but this is the most reasonably priced option with easy access to the sea. Ask for one of the garden rooms, the most recently renovated in the inn, which are close to the bocce court and fire pit on the front lawn.
2. Where to Eat
Pretend you’re in a camp mess hall and brave the crowds at the bustling Maine Diner, which is regionally famous for serving well-loved New England comfort food like seafood chowder ($6), lobster pie (market price), and crab cake sandwiches ($6.95). Though it may look like a tourist trap with its adjacent gift shop, its 30-year history, loyal clientele of locals, and vegetable garden set it apart from the average roadside spot.
Grab a seat on the outdoor patio at Pedros, a Kennebunk newcomer from the owners of local favorites Pier 77 and the Ramp. Take advantage of the daily happy hour specials (3–6 p.m.) like $5 margaritas and $3 fish tacos, but also try the more unusual braised mussels with grilled chorizo.
Sip the area’s best handcrafted cocktails at 50 Local, a causal bistro that manages to be farm-focused without feeling pretentious. The lineup changes daily (you’ll find a list of the day’s ingredients and their provenances on a floor-to-ceiling blackboard), but you can count on truffle-oil-laced macaroni and cheese ($10) and the burger topped with aged Cheddar ($10).
3. What to Do
Hike through the 24-acre Marx Preserve (look for the sign off Route 9, opposite a utilities pump station) and explore an ecosystem that’s relatively rare in southern Maine: salt marshes. Bring binoculars to spot birds like great blue herons and goldeneyes among the pines and hemlocks. For more hiking opportunities, follow the adjoining three-mile Bridle Path (access at 71 Sea Road), which goes inland and toward the sea, or check out the Rachel Carson Wildlife Refuge, home to many species including bald eagles and moose.
Get your sea legs at Goose Rocks Beach, one of the most popular places in town for stand-up paddle boarding. The relatively gentle waves are ideal for beginners and the long stretch of white sand, often rippled with tide pools, is a fine place to relax afterwards. You can book a one-hour private lesson with Aquaholics Surf Shop ($75), but if you prefer more traditional paddling, call up Coastal Maine Kayak (half-day rentals from $35), and they’ll deliver a single or tandem boat to you.
Bike a tranquil stretch of the 65-mile, ten-foot-wide Eastern Trail, which runs from South Portland to Kittery. The six-mile section between Kennebunk (access at the Kennebunk Elementary School, 177 Alewive Road) and Biddeford opened to the public in 2010, and has since become one of the area’s most popular biking routes because it’s shady and relatively easy. Take a break at the pond on the way back and spot deer and wild turkeys through the conifer trees.
4. Insider’s Tip
If you’re in the mood for a picnic, skip the crowded spots in town for a more secluded experience ten minutes away inside the Wells Reserve at Laudholm ($4 admission, which partially funds the Laudholm Trust). Formerly a working farm, this research site is home to grassy fields, estuaries, and a beach that are open to the public but never bogged down with crowds. Before you go, pick up sandwiches and drinks at HB Provisions, and be sure to give yourself enough time to enjoy the tranquil setting before the trails close at sunset.
5. Oddball Day
Take a break from hiking and biking to pamper yourself a bit, starting with a Kahlua-spiked coffee ($2–$3) and a homemade blueberry-lemon muffin ($2) at Chase Hill Bakery. Around 10:30 a.m., walk over the bridge in Docks Square to depart on a 90-minute cruise aboard Kylie’s Chance ($20), a classic wooden lobster boat. The captain will give you an informative overview of the area’s waters, including a good look at Walker’s Point, the summer home of former president George H.W. Bush. Back on land, line up for lunch at the ever-popular Clam Shack for the famous fried clams ($15.50 for a half-pint), followed by a scoop of artisanal ice cream at newly opened Rococo. Next, pick up camp-inspired gear at Daytrip Society, which sells vintage-style Maine T-shirts and funny merit badges. A mile down the road, stop into Spaces for bracelets made from marine gear and Turkish towels that make great picnic blankets. Afterwards, unwind in a private treatment room in the woods at TreeSpa, where you can choose from a selection of herb-infused oils for your hour-long massage ($130). Once you’re rejuvenated, explore the Galleries at Morning Walk, a collective opened this past May by local artists who sell paintings, photographs, jewelry, and handmade home goods. Finally, splurge on a four-course dinner ($106) at the White Barn Inn, where the handsome dining room is housed in two renovated barns and the service is doting. The menu is appropriately filled with indulgent items like truffles and foie gras, which you can match with selections from the extensive wine list.
For insider tips, check out a local blog written by the owners of the Maine Stay Inn.