Few would argue the merits of a long summer weekend in Portland, Maine — craggy coasts to explore, lighthouses to marvel at, a thriving local beer and cocktail scene, lobster every which way. But the math isn’t on your side, as you’d be far from the only one queuing up for any of that. Once summer rolls around, Portland hosts nearly 8,500 visitors. But if you wait until December, the number drops to less than half. Wait until after the holidays, and it’s likely emptier still, meaning Portland’s all yours — lobster and all — without the wait.
The Weather
Of course, to get the most out of Portland, you’ll need to get outside. While it’s cold in town — the temperature from December to March averages about 30 degrees — it’s not exactly arctic. You will need a decent coat, hat, gloves and maybe a gaiter to keep the chill off your neck. Snow might greet you, too, so insulated and ideally water resistant boots are a good idea (and yes, locals wear L.L.Bean). As far as outdoor adventures go, when the temperature drops, you have access to nearly as many activities as you would in summer, except for maybe paddling marshes.
Where to Stay
About a 15-minute car ride from the city’s airport, and even closer if you’re getting into town with Amtrak, the Press Hotel is centrally located on the peninsula and about a 10-minute walk from the old port area. Once home to Portland Press Herald, which relocated in 2010, the hotel pays homage to the building’s history with whimsical touches, like an art installation of typewriters in the lobby and a newspaper-like printout in the room that brings you up to speed on the neighborhood. The lobby houses the locally-sourced-obsessed Union restaurant, one of the best in the city with an underrated breakfast. The shakshuka comes with crusty bread that you should use to sponge up the tomato sauce like it’s a Sunday Italian dinner. Windows flood the first floor with light, making it a great way to spend a morning people watching, coffee in hand, from the in-house lobby bar Inkwell.
Here’s a tip: the Press is across bustling Congress Street from the stately Beaux-Arts city hall, which has a bell that rings hourly, so ask for a room towards Federal Street if noise keeps you up at night.
Where to Eat Lobster
While lobster season peaks between June and December, boats come and go from Portland all year long, so the iconic roll isn’t hard to come by. But not every lobster shack is open through the winter. If you’re strolling around the port, the best lobster comes from Luke’s on Portland Pier. This family-run business, with roots in nearby Cape Elizabeth, started in New York City before returning to Maine. The dining room is bright with views of lobster cages on the dock. If the wind is whipping off the harbor, Eventide Oyster Co., a couple blocks inland, adds brown butter to its lobster rolls. The dining room is smaller, but you can grab a seat at the oyster bar that’s topped with a hollowed slab of stone filled with ice and well-labeled bivalves.
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Coffee Runs
In a city that knows a good cup of java, Coffee By Design stands apart for the care they put into small-batch roasting, with two locations in the East Bayside neighborhood. Not too far away is Tandem Coffee Roasters, with sweet, freshly-baked goods to start your day. Seeing Tandem’s West End location in an old gas station might just be reason enough to head out for the 20-minute walk from the hotel.
Dinner
For burgers served with plenty of shredded iceberg lettuce (as they should be), thick old-school shakes and fries, head to Black Cow. Grab a seat by the windows to watch the foot traffic from the port on Exchange Street. Bar Futo’s Japanese menu has skewered meats — including one called Big Mag with a special sauce — and a range of small and large plates to share. If you’re in the West End area, Chaval is part French with some Spanish influences and has lots of sharable small plates. Split something snackable, like chicharrones, or go all in on heftier dishes like coq au vin.
What to Do Outside
Only about three miles across, compact Portland is walkable, provided you have a decent winter coat. If you’re near either end of the peninsula, there’s reason enough to get outside. Spy the stately Victorian era and early 1900s homes by walking the Western Promenade just off the Fore River. For bay views, the Eastern Promenade, on the other end of Portland, is a 68-acre park with paved walkways in the Munjoy Hill neighborhood, designed by Fredrick Law Olmstead of Central Park fame. Taking a ferry across the bay to one of Portland’s seven major islands is popular in summer but far less crowded in winter — it would most likely be you and the locals. Those who take a ride to Peaks Island can explore Battery Steele, a decommissioned WWII concrete fortification, with views out onto Casco Bay. Pack a flashlight because the light disappears once you get inside.
The multi-use space Thompson’s Point has a rink for skating just west of the interstate. But for a more local experience, bring your skates and head to Deering Oaks Pond within the park of the same name. Then on your way out of the park, walk to Holy Donut on Park Avenue for a potato donut that’s moist and fluffy enough to make you forget cake or yeasted versions. If you catch a warm spell and want to log some trail running miles, Robinson Woods Preserve is a 16-minute ride south of the city with just more than four miles of technical trails. The Harborwalk Trail is one of Portland’s greatest hits, taking you about six miles from East End beach along the coast south, over Casco Bay Bridge to Bug Light Park.
If your itinerary includes snow sports, Sugarloaf is 2.5 hours north of town for Alpine resort skiing above the tree line; Sunday River is about 90 minutes northwest. If you’re not into racing down a mountain, these resorts also offer Nordic skiing, snowshoeing and fat biking, which is a unique way to explore the trails. If you’ve packed your own gear, the 5,000-acre Pineland Farms in New Gloucester has room for snowshoeing, fat biking and sledding, all with a view of Mount Washington in New Hampshire.
What to Do Inside
If you want to duck inside for some warmth, Portland Museum of Art has an excellent permanent collection anchoring the Arts District. You might spy a Warhol, Monet’s waterlilies and plenty of Winslow spanning American, European and contemporary pieces. You could book a van-guided brewery tour on Fridays and weekends through Maine Brews Cruise or pop into the brewers at a more leisurely pace by visiting Long Pine Brewing, Belleflower Brewing and Rising Tide, all within a half mile. If you think craft beer works best with an activity, build an ecosystem you can take home at Terrarium. If walking around a New England port town in winter chilled you to the bone, a public sauna session at Washington Baths is an experience that can warm you up.
Tour the Lighthouses
Spend an afternoon visiting the lighthouses, which take on a different vibe come winter with rough seas and maybe some snow. Portland has six lighthouses spread over five sites (one has a pair of them), all within about 20 miles. Head out of the city to the furthest one away, in Two Lights State Park, then work your way back. If you’re short on time, Portland Head Light is the most iconic of them all and you can get right up to it, which isn’t the case for all of the lighthouses.
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