Are you reeling from the recent heat and humidity? One bowl of ice cream isn’t sufficient relief? Here’s a pub crawl-style guide to seven of the best ice cream shops on Route 302 between Windham and Bridgton. While the locations are ordered as if one was driving out from Portland, feel free to visit them in any order you choose.
FIRE AND ICE
This North Windham restaurant doubles as an ice cream shop and pizzeria, with specialties including New Haven-style pizza and rolled ice cream. Rolled ice cream, as served at Fire and Ice, is essentially ice cream converted into a solid, rolled-up shape, with whipped cream and toppings. Notable flavors include Rainbow Ice, Mud Pie, Crazy for Butterfinger and Mint Madness.
ICE CREAM DUGOUT
Located in North Windham, this outdoor shop celebrates two of America’s greatest summer staples: ice cream and baseball. The store serves more than 40 flavors of Shaker Pond ice cream, with baseball-themed specialty sundaes including Brookie of the Year, Strawberry Field of Dreams and The Hall of Fame, as well as beverage options such as the “Yankees Suck’er” extra thick frappé.
THE MOSQUITO

This Raymond ice cream shop is celebrating its 30th anniversary with a vintage sign depicting a mosquito licking a strawberry ice cream cone. The shop, whose interior resembles a lake house or a summer camp cabin, also sells sweatshirts and hoodies, which an employee said made the place feel “homely.” Notable flavors include Campfire S’mores and Chocolate Cookie Monster.
RAYMOND’S FROZEN CUSTARD
Confusingly located in Casco, across from the Raymond Casco Historical Society, this frozen custard stand is named for owner Raymond Dingley. The store is distinguished by the painted school bus outside, which serves as a dining area. The store has been in business for 22 years, and, according to Dingley, is one of just three frozen custard stands left in the state. Notable flavors include vanilla, chocolate and black raspberry every week, and five new flavors each week such as orange dream and maple walnut.
CAUSEWAY DAIRY BAR
One of two “dairy bars” in downtown Naples, this ice cream stand is owned by the Klimek family, who also run the Black Horse Tavern in Bridgton. The shop, which has a balcony overlooking Long Lake, also serves smash burgers, among other lunch items. Notable flavors include strawberry lemon sorbet.
LAKESIDE DAIRY BAR

Farther up the Naples Causeway is the Lakeside Dairy Bar. This location serves about 50 flavors, including toasted coconut, Cookie Curve-Ball, Fluffernutter, and marshmallow with peanut butter. One of the more notable flavors is Painkiller, a mix of coconut ice cream, rum-flavored sauce, and nutmeg, based on the owners’ time living in the Caribbean.
MAINE STREET CREAMERY
Serving downtown Bridgton, this ice cream shop has been in business for four years and serves a variety of flavors, including Black Raspberry Explosion, Moose Tracks and Hakuna Matata.
“We love our customers, we have the best customers in all of Maine,” said employee Addie Balabanis, whose family owns the shop.

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