Editors' picks across 8categories — the dock with the deepest channel, the winery with the view, the restaurant with the right wine list, the trail nobody's on at sunrise.
Restaurant in the 1901 Naples Casino building right on the Causeway, doing waterfront dining for more than forty years running. The menu mixes American, seafood, and a Mexican section that's stayed on the card longer than most single-cuisine competitors survive. Front-porch seating is the move for watching the Causeway's boat and foot traffic work through a July evening. Open seasonally, Memorial Day through late September.
Visit ↗Family-owned restaurant and bar built into Naples Marina on Brandy Pond, with a gas dock and slips so arriving by boat is as normal as arriving by car. Pub-style menu, live music some nights, and a deck that catches the Causeway's evening traffic from the water side instead of the road. Order in by boat and the marina staff will point you to a table.
Visit ↗Soft-serve and hard-scoop stand on Roosevelt Trail near the Causeway, one of several ice cream stops within walking distance of each other in Naples but the one locals name first. Long line by mid-afternoon in July; go before noon or after eight if the wait matters more than the crowd-watching.
Visit ↗Ice cream stand on Route 302 in Raymond known for portions bigger than the price suggests and a flavor board that changes through the summer. One detail worth knowing: they sell a plain-yogurt scoop called the Poly Dog for anyone who brought the dog along.
Seafood counter and taproom on Route 302 in Windham, fried oyster platters and fish tacos alongside a rotating beer list in an industrial-rustic room that reads more like a Portland spot than a lake-town one. Newer addition to the Windham strip and busier on a weeknight than most of what's around it.
Visit ↗Upscale pub on the lake's west shore with its own dock, so arriving by boat is a real option rather than a suggestion. Breakfast pizza and a lobster Benedict cover the daytime menu; the kitchen's Italian roots show up more in the dinner sauces than the name suggests. Lake views from the deck rather than just the parking lot.
Visit ↗Casco taproom at 333 Roosevelt Trail built from the legacy of Mike Bray's old Naples brewpub — Tor Moson picked up the recipes after Bray's closed in 2017 and reopened them here. Thursday through Sunday only, and pizza comes from Naples Homeslice next door since the taproom doesn't run its own kitchen. The rotating lineup runs from crisp session ales to bigger stouts.
Visit ↗The brewery the lake lent its name to, twenty minutes south in Gorham rather than on the water itself. Three friends — Kai, Tim, and Brad — opened the original brewpub in 1998; the Main Street tasting room now sits next to the production brewery with a wood-fired oven and a wide outdoor patio. Worth the short drive off Route 25 for the flagship IPA and the fact that it started the region's craft-beer run.
Visit ↗Maine's second-largest lake gets its most complete public access here — two campground beaches, Naples Beach and Witch Cove, plus a day-use area with more than five miles of mixed-growth forest trail along the lake and the Songo River. The Songo Beach Trail runs a flat 2.4-mile loop most of the way on packed gravel. Open year-round, 9 a.m. to sunset; cross-country ski the same trails once the campgrounds close.
Visit ↗Raymond's town beach on the eastern shore, thirty-eight acres with roughly 900 feet of sand shaded by white pine and a Snack Shack that covers the basics without a drive into town. The swim area is marked by buoys with no lifeguard on duty, so it draws a calmer crowd than the state park seven miles up the road. Connecting trails cover just under a mile if the kids want to move before or after the water.
Visit ↗A paved, gated road climbs 753 feet to an open summit on Quaker Ridge Road with a clear line to the White Mountains on one side and the lakes region, Sebago included, on the other. The gate opens May through October, Monday, Wednesday, Friday, and weekends only — check before driving up on a Tuesday. Restrooms and picnic tables at the top make it a legitimate sunset stop, not just a scenic pull-off.
Visit ↗West-shore marina at 28 Marina Road doing the full range — rentals, fuel, slips, engine service, and winter storage — for anyone based on the Sebago-town side of the lake near Nason's Beach and Long Beach. The practical choice when the plan is centered on the lake's western basin rather than the Naples end. Call ahead for rental availability on a July weekend.
Visit ↗Protected-cove marina in South Casco behind the Dingley Islands, close enough to Sebago Lake State Park's north end to work as the launch point for that side of the lake. Rentals, slips, fuel, an on-site mechanic, and a convenience store that covers what a cooler always runs short on. Calmer water here than the open basin further south, which matters on a windy afternoon.
Visit ↗A hundred wet slips plus a hundred fifty valet slots on Route 302 in Raymond, the marina built for a season-long relationship rather than a single weekend rental. Full service and fuel on site. The Raymond side of the lake runs quieter than the Naples Causeway scene a few miles north, and this is the marina that reflects it — less foot traffic, more boat owners.
Visit ↗Kayak, canoe, and paddleboard rentals and sales at 1311 Roosevelt Trail in Raymond, open late April through October with weekends-only hours after Columbus Day. The company delivers straight to a campsite or the nearest beach, which matters on a lake this size where the put-in isn't always where the rental shop is. Life jackets and paddles included in every rental.
Visit ↗Ninety-three-foot diesel-powered stern paddlewheeler docked right on the Naples Causeway, launched in 1982 as the replacement for the original Songo River Queen, which burned in 1981. It used to run through Songo Lock all the way to Sebago Lake until the fixed causeway bridge landlocked it in Long Lake in 2011 — today's cruises run the eleven-mile length of Long Lake instead. One- and two-hour narrated trips daily in season; walk-ups welcome when there's room.
Visit ↗Hand-operated lock on the Songo River at the north end of Sebago Lake State Park, built in 1830 and the last surviving lock of the Cumberland and Oxford Canal — one of the few hand-cranked locks still working anywhere in the country. Boats drop about four feet passing from Long Lake and Brandy Pond down into Sebago. Runs May 1 through October 15, nine to six, seven-fifty each way.
Visit ↗The bridge and the strip around it where Long Lake meets Brandy Pond — ice cream stands, the Songo River Queen's dock, and most of the town's boat traffic funnel through here. The current arch bridge went up in 2012, replacing a swing bridge that had opened for boat traffic since 1954. Walk it at seven in the evening once the day-trip crowd has cleared out.
Visit ↗Seasonal car ferry from Raymond Neck to Frye Island, a private, roughly thousand-acre island community in the middle of the lake reached no other way except private boat. Golf carts do most of the driving once you're on the island's twenty-two miles of dirt road. The ferry stops running when the ice gets too thick in late fall and doesn't restart until it clears in spring.
Visit ↗