Friday
Checking in and dining out

Start your weekend by settling in at The Press Hotel, the boutique hotel on Congress Street with 110 rooms and suites and a well-regarded on-premise restaurant, Union. The rooms are spacious, with high ceilings, wood floors, luxurious linens, and local artwork, and upper-floor rooms feature stellar views of Back Cove and Portland Harbor.

For before-dinner drinks, Cocktail Mary is a ten-minute walk from the hotel and has a small outdoor patio area. The East End bar also sells drinks to-go, including craft cocktails masterfully created by owner Isaac MacDougal. Try the Scurvy Snack, with white rum, pineapple gum syrup, lime, and caraway, and the Orchard Rye, with rye whiskey, Fernet Michaud, Meletti amaro, and apple juice.

Reservations are recommended for dining at Izakaya Minato on Washington Avenue, but walk-ins can put their name in for a table and go grab a drink at one of the nearby bars, breweries, or distilleries. Oxbow Blending and Bottling across the street has an outdoor courtyard with well-spaced seating and respectful patrons. String lights hang overhead, and there’s a crackling fire pit in the back. Guests sip beers and snack on food from Duckfat Friteshack, which has an ordering window in Oxbow’s patio, while others enjoy cocktails and cider from the neighboring bar, Anoche.

At Izakaya Minato, peruse the menu of Japanese small plates that are meant for sharing before deciding on your feast. Some dishes, like the Japanese fried chicken, are always on the menu, but keep an eye out for in-season specials like the uni spoon, with Maine sea urchin, raw quail egg, ponzu, and tobiko.

Saturday
Exploring by foot and a Munjoy sunset

Just up the block from the hotel is Little Woodfords, a coffee shop in a teeny-tiny pink and white brick building at the corner of Congress and Franklin Streets. After grabbing a coffee, continue up Congress to the Eastern Promenade for sweeping views of Casco Bay.

Head back down Munjoy Hill for a quick bite to eat. Forage Market’s wood-fired bagels are delicious, crispy on the outside and soft inside. Nearby on Washington Avenue, The Cheese Shop of Portland sells sandwiches to go, including a deceptively simple sandwich with cultured butter and Benton’s country ham on a fresh baguette.

Pack your snacks and drive 15 minutes to Oat Nuts Park, part of the Presumpscot River Preserve. The trail from the North Deering park weaves through the woods to the edge of the Presumpscot River and down to Presumpscot Falls. The path, managed by Portland Trails, is well maintained and easy to navigate.

On your way back to downtown, stop in at Maine and Loire on Washington Avenue to browse the shop’s vast selection of natural wines. The store’s COVID-19 precautions allow only one customer at a time, so you’ll be able to ask the staff plenty of questions in your search for the perfect bottle (perhaps a Furlani “Joannizza” or Casalpriore Lambrusco).

Park on the Western Promenade to see what might be the city’s most scenic neighborhood: the West End Historic District. Stroll through the Western Cemetery and get lost in the neighborhood’s charming side street for views of grand Victorian homes and other historic structures.

For lunch, drive downtown to Leeward for fresh pasta, dessert, and cocktails to-go. Takeout has never looked as beautiful as it does here. Get some of the house-made pasta, like the ribbon-shaped mafaldine with bolognese sauce, and perhaps the burrata and roasted beet salad to enjoy back at your hotel room.

The best sunset in Portland can be seen at North Street’s Fort Sumner Park on Munjoy Hill. The view of the whole peninsula, with Mount Washington and the White Mountains outlined against the fiery sky, is breathtaking, and the city lights twinkle as the sun fades. Driving back into town along the Eastern Promenade will reward you with more sunset views over Casco Bay.

A block from The Press Hotel on Exchange Street, Highroller Lobster Co. is perfect for a lively late dinner or bite to eat. Sitting on the back patio, you can order and pay at your table using your phone. Finish your day with shrimp cocktail, oysters, fries, and, of course, a lobster roll—try the charred pineapple mayo for a slightly different take on the classic.

Sunday
Waterfront stroll and a brewery pit stop

After checking out of the hotel, head into the Old Port on foot. The recently opened Mount Desserts Pie Company offers an assortment of savory or sweet hand pies to go, including strawberry rhubarb and raspberry with brie. Continue down to Wharf Street’s cobblestones for a coffee from Higher Grounds (locally roasted by Speckled Ax), then along Commercial Street and the working piers on the water’s edge. Between Portland Pier and Custom House Wharf is a popular spot to take a photo of the backside of Harbor Fish Market. Pass through the Casco Bay Lines ferry terminal and enjoy your flaky hand pies and coffee on the wide Maine State Pier.

For another stroll, drive about ten minutes across town to Evergreen Cemetery. Established in 1854, the state’s largest cemetery is a National Historic Landmark and features long, winding carriage paths, footbridges, gardens, and over 40,000 monuments. If you find the Rines family mausoleum, check out the stunning stained-glass window and its kaleidoscopic patterns.

No trip to Portland is complete without visiting the city’s celebrated breweries, and many are found in East Bayside. Austin Street Brewery and Rising Tide Brewing Company are side by side on Fox Street and have large patios for enjoying their beer on-site. On your way out of town, take a detour up Munjoy Hill to the Eastern Promenade for a final look at Casco Bay. You’ll see seagulls flying overhead as the water sparkles and hazy clouds creep over the islands in the distance. It’s the perfectly peaceful and picturesque close to a weekend in Portland.