Craft beer, craft coffee, and history around every corner: Maine’s liveliest city is reinvigorating New England’s classic traditions.
Be sure to pencil in some time on Portland’s buzzy waterfront. / Photo by Sean Pavone/Getty Images
From the food and history to the waterfront location, Portland is a place Bostonians will immediately recognize as reminiscent of home. But over the past couple of decades, the city has developed its own distinct old-meets-new flavor that makes it a must-visit destination in its own right, with a reputation as a burgeoning hot spot teeming with creatives, boutiques, and, of course, a killer food scene.
After your quick journey up the coast, fuel up on malt iced coffee and gooey, cinnamon-y sticky buns at Tandem Coffee + Bakery in the heart of the West End, one of the best-preserved Victorian neighborhoods in the country. When you’re ready to hit the pavement, head over to the East End’s Portland Observatory, where you can take in panoramic views of downtown and get your bearings. As the only remaining historical maritime signal station in the country, it’s an ideal place to soak up elevated views as well as a quick history lesson. From there, it’s a quick stroll over to the Eastern Promenade, a 68-acre waterfront park designed by the Olmsted Brothers, who are known for creating Boston Common.
You’re going to need plenty of long walks, after all, to work off the abundance of fabulous food across the city. Don’t miss Café Louis, a Costa Rican and Caribbean restaurant with inventive dishes such as fiddlehead empanadas stuffed with Cabot cheddar cheese; Fore Street, the haute farm-to-table destination restaurant that first ignited Portland’s dining scene 25 years ago; the Honey Paw, a “nondenominational noodle bar” from the folks behind Eventide Oyster Co.; and the new Brickyard Hollow Brewing Company, for craft beers and pizzas topped with Maine blueberries and smoky pulled pork.
If you have time after your culinary journey, consider hopping on a cruise with Portland Schooner Co., which offers two-hour tours of the harbor and Casco Bay in Maine-built windjammers that are listed on the National Register of Historic Places. After all, on a warm autumn evening, few things are more memorable than seeing the lights of the city from the water.
The new rooftop bar at Canopy by Hilton Portland Waterfront / Photo courtesy of Canopy by Hilton Portland Waterfront
Hop in the car and you’ll be in Portland in two hours, or you can kick back on Amtrak’s Downeaster train and get there in two and a half.
If under-the-radar is your thing, check into Blind Tiger, a restored 1823 guest house tucked away in the residential West End, and wake up feeling like a real Portlander. If hip and happening is more your speed, book the new Canopy by Hilton Portland Waterfront, where the rooftop bar is one of the city’s latest hives for an outdoor tipple.