Where to eat. Where to drink.

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.

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.

Causeway restaurant doing seafood and sandwiches with a straightforward lake view rather than a fine-dining pitch. Full bar, a menu built for a family that wants something besides pizza, and a location close enough to the Songo River Queen's dock to make it the pre-cruise dinner option.

Tavern in a historic farmhouse a few minutes off the Causeway, the kind of neighborhood pub-grub spot that draws a local crowd rather than the day-trip traffic downtown. Simpler and quieter than the waterfront restaurants, which is most of the appeal on a night when the Causeway itself feels like too much.

Irish pub near the Causeway serving fish and chips, steaks, and burgers, with live Celtic music some weekends — the one place in Naples doing that specific genre of pub, and it plays it straight rather than as a gimmick. Full bar; the dessert case gets mentioned almost as often as the entrées.

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.

Seafood spot on Route 302 in Raymond doing lobster rolls, fried plates, and chowder without the Causeway markup. Straightforward counter-service setup, better for a fast dinner on the way back from the boat launch than a sit-down occasion.

Mexican restaurant in a repurposed silver diner car on Route 302, margaritas poured generous enough that they're most of what regulars mention first. Casual, loud on a Friday, and one of the few non-seafood, non-pizza options on the Raymond stretch of 302.

Seasonal restaurant on Frye Island, formerly Frye's Leap Café, reachable only by the car ferry from Raymond Neck or by private boat. The kind of dinner that requires planning around the ferry schedule rather than a reservation time, which keeps it from ever feeling like a tourist stop despite the island setting.

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.

Farm-to-table restaurant on the Windham strip doing a more polished version of comfort food than the chains on either side of it. Reservations help on a weekend; walk-ins work most weeknights.

Steakhouse and seafood spot in Windham for the night the group wants a real dinner rather than another Causeway burger. Traditional American menu, dependable rather than adventurous, which is exactly the point for a week-long rental crowd with mixed tastes.

Diner on the Windham strip open for the classic breakfast-and-lunch shift, the reliable stop before a beach day when the rental kitchen isn't stocked yet. Nothing reinvented here, which is the appeal.

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.

Wine bar and small-plates room in the town of Sebago on the lake's quieter west shore, built for a couples' dinner rather than a family table. Live music some nights, and a wine list that goes past the usual lake-town shelf. Reserve ahead in summer; this isn't a walk-in kind of room.

Resort restaurant at Point Sebago on the lake's northeast side, seasonal and built around the Beach Pavilion rather than a standalone dining room. Works best if you're already on the resort property for the day rather than driving in specifically for dinner.

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.

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.

Up Route 302 past Naples in Harrison, a farmhouse taproom with up to ten beers on tap plus wine and cider for anyone not drinking beer that day. Live music fills the room Saturday evenings, trivia runs Monday nights, and a comedian takes the small stage the first Thursday of the month. Open Friday through Sunday only — check the tap list before making the twenty-minute drive up from the Causeway.