Portland is an ideal base for a weekend of active exploring, with numerous trails for running, biking, or walking and more adventures activities like surfing only a short drive away.
My girlfriend, Caroline, and I live in Portland, but this weekend it’s also the location for our 36-hour getaway. Maine Media Collective’s office is located near Portland’s eastern waterfront, so our first stop is at Shipyard Brewing Company’s recently expanded tasting room. We each order Finder, Shipyard’s take on the popular hazy New England-style IPA. It’s my new favorite from Maine’s largest brewery.
We check in to our accommodations for the weekend, the classic Portland Regency Hotel and Spa. After dropping our bags in our room, which has a private deck that looks down Market Street toward the water, we walk toward the Arts District for Portland’s First Friday Art Walk.
Maine College of Art has its third annual Zine Fair on display with stacks of colorful DIY publications on tables and some strung- up on clothespins and wires. Next we walk to the Portland Museum of Art, where the 2018 Biennial is on display through June 3. It features a range of more than 60 works by 25 artists connected to Maine.
We arrive early for our reservation at Sur Lie, so Caroline has a glass of grüner veltliner, while I enjoy the Hired Gun, a bourbon-based cocktail with Pimm’s, cinnamon syrup, absinthe, and Coastal Root bitters. We both order the tapas- style tasting menu, which consists of a variety of small plates that display the talents of chef Emil Rivera, including a standout sweet pea hummus.
For a nightcap, we stop in to the Armory Lounge in the lower level of the Regency. There are few places in Portland as fitting for sipping on a classic cocktail as a corner of the Armory in one of its armchairs. Our drinks—a dirty martini for her and an old fashioned for me— are perfectly executed, boozy, and ice cold.
After planning our day out in bed with a carafe of hot coffee, we don our running gear in preparation for a windy run along the water. Our route takes us down to Commercial Street and along the Eastern Promenade Trail. We stop at Coffee By Design on India Street after our run for more coffee and glazed treats from the Holy Donut.
We venture off the peninsula and just outside the city to visit Mackworth Island, which is connected to Falmouth by a causeway. We follow the one-and-a-half-mile trail around Mackworth for views of Casco Bay’s islands and fairy house villages constructed just off the dirt path in the woods.
Ready for something more substantial than a doughnut, we head off the peninsula to Rose Foods for bagels with lox and cream cheese. Back in the Old Port, we walk toward Commercial Street. We take some photos of the Instagramable back side of Harbor Fish Market, then visit another Portland institution, J’s Oyster. These large oysters are best enjoyed with a healthy dollop of cocktail sauce and a squeeze of lemon and washed down with a beer.
The Old Port has numerous independent retailers, and we begin with LeRoux Kitchen, sampling a selection of olive oils and vinegars and checking out the vast selection of Le Creuset cookware. Portland Dry Goods has a collection of quality and stylish men’s and women’s clothing and accessories, including beautiful and masculine necklaces and bracelets from local metalsmith Cat Bates. At Gus and Ruby Letterpress, we find a charming and whimsical selection of cards and other paper products, pens, candles, jewelry, and more. Across Exchange Street, Peyote Moon offers women’s clothing and accessories, curated from small-batch companies.
After fueling up with Bard Coffee, we walk toward the East End for an afternoon bite and drinks. The Honey Paw consistently serves some of Portland’s best and most- interesting dishes, and our rare beef salad and lobster wontons don’t disappoint. We decide that the half-dozen oysters we ate earlier weren’t enough bivalves for the day, so we head toward The Shop Raw Bar and Shellfish Market on Washington Avenue. We wash down a dozen more oysters with glasses of dry white wine on tap.
Inner Washington Avenue is home to some of my favorite places to eat and drink, so we stay in the neighborhood for dinner. Izakaya Minato, open for just over a year, is cozy and hip, with Japanese gastropub-style small plates. The omakase tasting option might be the best $30 you will spend in Portland.
We schedule massages for our last morning at the Regency. The full-service spa with a Jacuzzi, saunas, steam rooms, and a fitness room is below the hotel, an oasis tucked in a busy section of the Old Port. The signature Regency Massage incorporates Swedish and deep-tissue techniques, hot stones, and aromatherapy. Spa director April Rossignol is warm and welcoming, offering recommendations for treatments.
We continue our laid-back morning with brunch at Little Giant in the West End with our friends Kit and Lennie. The space is bright and comfortable. Little Giant, which also offers dinner seven nights week, has one of my favorite cocktail menus, especially at breakfast. My Nashville hot chicken and waffles is deeply satisfying and the perfect end to our 36HRS in Portland.