3 Best Restaurants in Bayside, Portland

The design and overall atmosphere here—part rustic Maine hunting lodge, part chic ski Aspen lodge, all beneath soaring ceilings and in front of a real roaring fire—keep crowds coming back, but the craft beer is very good (pale ales, IPAs, pilsners—you name, they’re pouring it), as are the cocktails (the carefully made spirits include a slightly sweet vodka made from corn; a bourbon, and a gin, among others). And, the food deserves kudos, too—snacks like duck fat cornbread with hot honey, and mains, like the lobster mac ’n cheese with Boursin, do not miss. There are three other locations in Kennebunk, Biddeford, and Wells.

A local institution (it's been here since 1949, and Portland's historic preservation department even helped restore it), Portland's beloved gem housed in a Worcester dining car is as authentic as they come. The menu's full of diner staples—lots of homemade pies, daily soups, big breakfasts, BLTs, and thick specialty milkshakes (in flavors like grasshopper and s'mores). The unusually friendly staff—when they're not swamped—will happily dole out advice on spots to visit in town. Expect crowds in the summer, accommodated by extra seating in the back, built off the car. 

A regular stop for pie lovers around the city, Two Fat Cats bakes up delectable bourbon pecan, sour cherry, and coconut cream masterpieces. Meanwhile, the bakery’s whoopie pies rely on light and fluffy, hand-scooped chocolate cake batter and a filling that’s based on whipped vanilla buttercream, not the more typical marshmallow. The signature pie is made with wild Maine blueberries sourced from Maine-based and family-owned Wyman's. A second shop is located at 740 Broadway in South Portland.