Portland in 48 Hours
With a thriving food scene, walkable neighborhoods built for exploring, and plentiful water views, Maine’s biggest city has much to offer the weekend traveler.
Cobblestones and cocktails
Start your weekend in Portland with a stroll around the Old Port, home to historic buildings and a working waterfront. Sturdy footwear is recommended for walking its cobblestone streets. While you may be visiting for the boutiques and cafes, you will find cultural landmarks dotted throughout Portland, like Lobsterman Park—a cobblestoned square at the intersection of Middle and Temple Streets with a sculpture of a lobsterman and his catch— showing the roots of Maine’s largest city before it became known as a hub of world-class restaurants.
Newly opened in summer 2021, the Canopy by Hilton Portland Waterfront hotel on Commercial Street serves as an invigorating home base for the weekend, with 135 rooms, plenty of chic sitting areas such as a tranquil, glassed-in library space, easy access to the gym (or, if you stay in a “Fitness Room,” an en suite Peloton gym), and eye-catching interior design throughout, including a moss wall installation in the lobby. Walk past the hotel’s cafe and bar, Salt Yard, and take the elevator to the top floor to start your evening with drinks and appetizers at Luna Rooftop Bar, an indoor-outdoor space featuring sweeping views of the waterfront.
Now it’s time to hit the town. Make your way to the Portland Museum of Art (PMA), which has free admission for the general public on Fridays, and wander the galleries to view the permanent collection, including works by Winslow Homer, Dahlov Ipcar, and Pierre-Auguste Renoir, as well as the current exhibitions. North Atlantic Triennial: Down North, a collaboration with museums in Iceland and Sweden that the PMA museum is calling the first exhibition devoted entirely to contemporary art of the North Atlantic, will be on display starting February 18.
It’s a short walk over to dinner at Wayside Tavern, located in a space adjacent to the Francis Hotel. The restaurant boasts an extensive wine list, delicious cocktails, appetizers and larger plates, and a cool-cozy vibe with bar and couch seating. On the way back to the hotel, stop for a nightcap at the Jewel Box (formerly the Bearded Lady’s Jewel Box), a cocktail bar with funky ambiance and fun drink options, such as the Dank Ocean, which delivers a smooth kick with smoky scotch, crème de menthe, and green bell pepper juice.
Breweries and boutiques
Leave the peninsula for a morning walk around the Fore River Sanctuary, an 85-acre preserve on the western edge of the city with over five miles of trails for walking, trail running, and mountain biking. Make your way to Jewell Falls, Portland’s only natural waterfall, for a little bit of forest bathing before you dive into the day.
On the way back into the heart of the city, stop by community hub Thompson’s Point, where you can grab a quick bite to eat at Rosemont Market and Wine Bar, a cup of coffee from Rwanda Bean, or if it’s a little later in the day, a drink from Bissell Brothers Brewing Company or Stroudwater Distillery. If you’re traveling with little ones, the newly opened Children’s Museum and Theatre of Maine is a must-visit for imaginative fun, and the nearby open-air skating rink is a winter favorite. Plus, the International Cryptozoology Museum, which focuses on unknown or hidden creatures like sea serpents and Bigfoot, will leave your head spinning.
You’ve held off long enough—it’s finally time to hit the shops. Stop by Mainely Noods, a noodle shop on Congress Street, for a quick boost of energy, and then make your way to Ember, a collaborative retail space featuring handmade ceramics from Campfire Pottery and jewelry and apparel from lifestyle brand Mulxiply. Head to the heart of the Old Port to check out boutiques like Blanche and Mimi, Gus and Ruby Letterpress, and Fitz and Bennett Home, and smell the spices at cooking store Skordo to get your taste buds tingling. If you need a quick pick-me-up, stop by Bard Coffee’s walk-up window, or grab an early dinner at Crispy Gai, known for Thai-inspired fried chicken, inventive cocktails, bright decor, and an exceedingly selfie-friendly bathroom mirror surrounded by neon lights, designed by Portland artist “Neon Dave” Johansen.
Round out your day with a trip to the East Bayside neighborhood, known as a breeding ground for newcomers to Maine’s beer and spirit scene. Check out spots like newly opened Belleflower Brewing; Portland Zoo, a beloved locals’ bar; and Après, the hard-seltzer tasting room in East Bayside. Then clear your head on the walk over to West Bayside for a rousing game of bowling at Bayside Bowl, which features a rooftop bar with 360-degree views of the city. Finish up the night with appetizers and drinks at the stylish Batson River Brewing and Distilling, or grab a final beer at Banded Brewing, with standout brews like Charms and Hexes and Gourd Lord on draft.
Savory snacks and ocean views
Get your blood pumping on your final morning in Portland with a run around Back Cove, a 3.6-mile loop with generous views of the Portland skyline. Stop by Coveside Coffee post-run for a pastry and a warm chai, and be sure to admire the mural on the outside by artist Tessa Greene O’Brien of Better Letter Hand Painted Signs. If you’re craving something a little more health promoting, Blake Orchard Juicery on Forest Avenue features smoothies and raw juices geared toward gut health.
On your way toward Washington Avenue stop by Print: A Bookstore to browse the extensive array of works by Maine authors in addition to a top-notch selection of fiction, cookbooks, and memoirs sure to please any bookworm or gourmand. You’ve likely worked up a healthy appetite, which is good news because restaurants like the recently New York Times– recommended Cong Tu Bot, Tex-Mex stand-out Terlingua, and hoagie heaven Ramona’s are within walking distance. Plus, shops like the knife store Strata and fermentation hub Onggi will keep you on your culinary toes. End your trip with a stroll along the Eastern Promenade Trail, where you can watch sailboats and fishing trawlers glide across Casco Bay, hunt for sea glass on East End Beach, and take in the sights and sounds of Maine’s biggest city.