Summer Weekend in Portland, Maine | Weekend Away

For the past few years, I’ve hosted summer travelers in the guest room of my house in Portland’s West End. It’s pretty much the perfect side hustle for a writer—pandemic notwithstanding—because I can stay in my natural state, i.e., my pajamas, while using my guests to vicariously explore my beloved hometown, which is also the hometown of my mother and my grandmother before her. My favorite part of the whole thing is scribbling down a few quick sightseeing suggestions based on what I’ve learned about my guests during check-in. My partner rolls his eyes at my excitement, but he’s from away, so he just doesn’t get it. Portland’s special. Of course I want to share it. It’s creative, walkable, socially conscious, and immortal.

Portland’s seal portrays the mythic phoenix rising from the ashes, a reference to the fact that Portland has been burned to the ground no fewer than four times—most notably in 1866, in an epic July 4 conflagration known as the Great Fire, which probably began with a firecracker or a cigar tossed carelessly in a waterfront warehouse and ended with 1,800 homes and businesses leveled from Commercial Street to Back Cove. (Walk around and you’ll see the aftermath: Victorian buildings built of fireproof brick or stone, per a post-fire town ordinance.) We rebuilt. Our motto, after all, is “Resurgam.”

Some orientation: Think of the topography of Portland’s peninsula as a saddle—a hill on either side with the Bayside, Downtown, and Old Port lowlands in the middle. The peninsula is about three miles long and includes the West End, Parkside, East and West Bayside, the Arts District and Downtown, the Old Port, and the East End. This city center is bookended by the Western Promenade and Eastern Promenade parks, both laid out by famed landscape architect Fredrick Law Olmsted, designer of New York’s Central Park. I’ve focused my suggestions on the peninsula not because there aren’t wonderful things to check out off-peninsula (Portland Head Light, I see you), but because the area is Portland’s historic, walkable, bikeable, Uber-able locus of activity, and if you have just 48 hours here, it’s small enough to really get to know. If I had one weekend in my beloved “city by the sea,” here is where I’d go, and what I would want to do.

Summer Weekend in Portland, Maine

FRIDAY

The West End & the Arts District

The West End features some of the city’s grandest mansions, built in the 19th century by a wealthy merchant class that wanted to settle the peninsula as far away as possible from what back then was a fish-fumed Old Port filled with rowdy sailors. Experience a piece of that elite exodus with a stay at The Francis, a boutique hotel located in an 1881 mansion designed by one of Portland’s most prolific architects, Francis Fassett, for the dry-goods merchant with the awesome Victorian moniker Mellen E. Bolster.

(Rather be centrally located? Try the Press Hotel, a sleek Old Port spot dressed up like the set of Mad Men and located in the historic brick-and-stone former home of the city’s daily newspaper, the Portland Press Herald. For a hip, contemporary take on Victorian-era lodging, check out the West End’s Blind Tiger or Parkside’s The Mercury.)

After checking in, stroll east down Congress Street past Longfellow Square (tip your hat to the statue here of Portland’s beloved bard Henry Wadsworth Longfellow) toward the shops and galleries in the Arts District, anchored by the Portland Museum of Art. Grab a boost if you need it at the hole-in-the-wall with the best brew in town, the award-winning Speckled Ax (if you’re up for a bit more of a trek, Speckled Ax’s airy new second location on the east end of Commercial Street has what might be the best breakfast sandwich in town/on the planet), before meandering around Portland Flea-for-All, a sprawling vintage furniture, clothing, and local crafts shop that is a favorite among local aesthetes.

For dinner, head back to the West End haunt Chaval.

With just enough mirrored wall mosaics to add a boozy Golden Girls vibe to the distressed-wood interior, Chaval is known for its delicious farm-to-table Spanish and French food and its array of vermouths and sherries, the latter of which can be sipped, per tradition, via the Sherry Luge: a halved length of roasted bone served with Chaval’s bone marrow appetizer.

SATURDAY

Peaks Island, East Bayside & the Old Port

Morning! Time to roll out of bed at The Francis and stagger across the street to flop face down into a sticky bun at famed Tandem Coffee & Bakery on Congress Street. Everything here is delicious and the coffee ranks among the best on the East Coast, so yeah, the long line is worth it.

After fueling up, head across town to the far end of Commercial Street to hop the Casco Bay Ferry to Peaks Island, the closest of the city’s year-round island neighborhoods. The 20-minute ferry ride is a nice on-the-cheap cruise of the bay. (Another option is the ferry’s mail boat run, which hopscotches four other islands farther out in the bay.) Once on Peaks, swing by Hannigan’s market for snacks and travel tips from owner Bob Hannigan before you rent a bike or golf cart from one of the handful of merchants close to the landing.

Spend a couple of hours exploring the century-old neighborhood and its beaches, forts, and lookouts, plus that eccentric homage to the mundane, the Umbrella Cover Museum. Then hop on the ferry and come back to one of the most acclaimed foodie towns in the country.

Head to the east side of town and Washington Avenue at the base of Munjoy Hill (between Cumberland Avenue and the highway). Start with lunch at Red Sea Restaurant, a no-frills Ethiopian and Eritrean eatery with delicious made-from-scratch fare, and for dessert, check out the charmingly conscientious vegan ice cream shop Sticky Sweet around the corner, or mosey down the street to other delicious nosh spots like Forage Market (yummy sandwiches and wood-fired bagels), Ramona’s sandwich shop, and the Shop raw bar.

Along the way, peruse the artful locally owned shops you’ll find on this stretch of Washington Avenue, including Venn + Maker, with its elegant selection of Maine crafts and home goods, and Strata, a top-notch kitchen knife sharpener and supplier whose international selection includes a few gorgeous Maine-made offerings.

If you hit the shopping wall, hike a couple of blocks up Congress Street to one of my favorite historical spots, the Portland Observatory. Built in 1807 by entrepreneur Captain Lemuel Moody, the 86-foot-tall building was used as a communication tower for a port that at the time was the largest on the eastern seaboard. A tour of the observatory will whisk you back to the maritime heyday of Port City, with a bonus view on a clear day all the way to New Hampshire’s White Mountains.

You have had a full day and now it’s time for dinner. Head to the Old Port, where a Saturday evening in summer is always a scene. Leave time before your meal to swing by the meticulously curated Portland Trading Co., which bills itself as a modern general store. Check out the handmade household items that have been sourced (and in the case of the clothing, designed) by owner and local fashion plate Kazeem Lawal.

Then snuggle into a spot at the cozy fine-dining lobster-and-fish stalwart Street & Co., but make sure you save room for dessert around the corner at the sarcastically named Gross Confection Bar, where accomplished pastry chef Brant Dadaleares creates inspired, Instagram-worthy, and altogether un-gross masterpieces. By the time the sugar rush hits you, the Old Port should be buzzing, too, with live music in every bar and on every patio, so wander the streets and see what intrigues you.

For an iconic nightcap, stop at the Top of the East at the Westin Portland Harborview, on High Street. In 2013, the Westin finished its renovation of the city’s oldest hotel, the Eastland, which was opened in 1927. The Top of the East has been the hotel’s rooftop bar since 1963 and features one of the best views of the city via floor-to-ceiling windows. Head there via the elevator in the main lobby, “R” floor, and end the night with the sight of Portland twinkling below.

SUNDAY

The East End

Follow the morning sun to the Eastern Promenade, the Western Promenade’s prettier sibling (even this West Ender has to cop to that fact) thanks to its stunning view of Casco Bay and the islands. To get there, head across town via Congress Street to Munjoy Hill. En route, consider popping into the Belleville to sample the buttery croissants by couple Amy Fuller and Chris Deutsch, who learned to bake in Paris.

You’ll want to leave some room, though, because there’s plenty of great grub to be had on the Eastern Prom.

Sunday brunch brings out the crowds for some of the city’s best food trucks, including Falafel Mafia and Mr. Tuna (yes, sushi from a truck can be delicious), but who are we kidding—most of us are here for the melt-in-your-mouth mini doughnuts of Eighty 8 Donut Café. Picnic on the sprawling lawn, chase the kiddos around the playground, or gaze at the bay and Fort Gorges.

You might see kayakers and paddle boarders cruising the water; if you’re motivated, rent the necessary gear at Portland Paddle, next to the beach at the base of the hill. Otherwise, just take the opportunity to chill and reflect on all you’ve seen, done, and tasted, east, west, and everything in between. That’s what I’d do. 

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