For years we’ve visited Portland, Maine in summer and relished its crisp salt air, blue skies, coastal charm and delicious food. Every time, we like it so much that we pore over real estate websites and catalogs to see if some perfect house might entice us to move there. And every time, we remember that Maine gets very cold and snowy in winter, and that we do not like cold. The cute clapboard houses that look so delightfully airy in summer seem like they would let the cold winter sea air blow right through. The cold was a deal-breaker. Or so we thought.

This year we challenged ourselves to try Portland in winter to see just how tough it would be on our tender southern temperaments. And to be honest, we were charmed. Granted, we happened to choose a weekend when the temperature eased above the freezing point, but the city was just as lively and lovely as in summertime. We just had to add a few layers of clothing.

In the city center by the old port, young art students mix with old salts, new bohemians with old money, classic New England style with the sharp modern lines of new construction. That fellow with the plaid shirt and bushy beard might be a lobsterman, an urban farmer, an art student, or a stock broker.

Shopping in Portland

For a fan of quirky, vintage clothing and cute modern design, Portland is a wonderland.

Pinecone and Chickadee began as a place for husband and wife team of Noah DeFilippis and Amy Teh to sell their adorable silkscreened products, and has blossomed into a showcase for local designers and a tightly curated collection of vintage pieces. We probably spent an hour there soaking it all in. 6 Free Street. Open Monday to Saturday 10 to 6, and Sunday 11 to 5. You might also want to try Little Ghost at 477 Congress Street, or Find at 16 Free Street.

If you want more, and we did, Portland Flea-for-All located just a few blocks away at 125 Kennebec Street is open Fridays from 12 to 5, and Saturdays and Sundays from 10 to 5, with four floors of vendors of curated collections. Dinnerware to dinner wear, shabby chic to mid-century modern, and plenty of vintage L.L. Bean.

Portland Architectural Salvage is in the same building, and takes it up a notch or three. Massive architectural salvage and furniture source. Need doorknobs or light switches for your traditional Maine home (or wannabe?). Or maybe a vintage leather suitcase? How about a farm table, or a set of vintage metal lockers. They’ve got you covered.

Eating in Portland

My goodness, Portland has some delicious food. We knew we wanted some oysters, but we learned an interesting lesson on our last trip to Portland. When locals eat oysters, the oysters aren’t local. We had gone in search of an old-style local oyster bar, and J’s Oyster at the pier fit the bill. A definite divy departure from the upscale joints in the city center, J’s offers oysters, lobster, clams, and cold beer, and little else. What surprised us was that when we ordered a dozen oysters, they came from our home river in Virginia, not the local Maine waters, because the Maine oysters are too expensive for their regulars, they said.

If you do want to sample Maine oysters, and not just the Maine oyster bar tradition, Eventide Oyster Co. is the place to go. They also focus on the oyster, but not to the exclusion of everything else. Our teenagers were not so interested in the raw oyster experience we craved, but the lobster roll was a perfect option for them. The chick pea fries and house made potato chips even brought a smile to their sullen teen lips. As the cold local beer did to ours.

A tour of Maine via oysters at Eventide

Duckfat, named for the perfect vehicle for frying potatoes, bills itself as a small sandwich shop, but that doesn’t seem like quite the right description. If I say that french fries and milkshakes are a big part of the menu, you might get the wrong idea. We are talking poutine, gelato floats, roasted pork belly panini… just take a look at this menu and tell me you don’t want to just move in and eat your way through it. It is truly a den of deliciousness, and it is the perfect spot for a family with teenagers. Or at least this one.

If duckfat and oysters get a big thumbs down from your crew, let’s head on over to the pizza and ice cream category. Flatbread Pizza Company is one of the few places you can eat right on the waterfront, and its pizzas and beer are simply scrumptious. The pizza oven is a centerpiece of the dining room, warming and entertaining the diners all around. Watch the pizza makers toss the dough in the air and guess which one is yours. Ingredients are locally sourced wherever possible, and servers are attentive.

As for ice cream, even in winter there’s room for this. Gelato Fiasco, just a block up from Flatbread Pizza Company, is a friendly spot, offering tastes of any of their creamy gelati before you order. Be sure to try the Sweet Resurgam flavor, made from burnt sugar and roasted almond gelato. The flavor is based on the motto of the city, which means “I Shall Rise Again,” adopted by the city after numerous fires destroyed much of the port city. I highly recommend the affogato, a scoop of gelato with a shot of espresso poured over it. Resurgam, indeed, with a caffeine and sugar buzz.

Drinking in Portland

Because this just wouldn’t be All Over the Map if we didn’t mention the healthy craft beer culture in Portland, here are a few adult-beverage-related outings you can take with your kids.

There are quite a few local breweries offering tours, but the most family-friendly, and also the most central, is the Shipyard Brewery, located at 86 Newbury Street in Portland. They offer free tours (really, a video tour and a peek at the bottling line) daily on the hour, and include tastings not only of their beers, but Capt’n Eli’s sodas for kids.

The Urban Farm Fermentory, tucked into the back of an industrial park, offers tastings of its many flavors of cider and kombucha, the fermented tea drink, at its small bar. The brews (only slightly alcoholic, at 1.5% for most) are infused with locally sourced flavorings, like basil, ginger, and chaga, a fungus found on the birch tree in Maine. The bartender is very knowledgable about the brewing process and the health benefits of her products. You can also purchase quart jars full of the stuff to take home. Under the same roof you’ll find several other food offerings on some days (check websites for current hours): Swallowtail Farm Creamery & Apothecary, Pure Pops, and Maine Pie Line.

Kombucha tasting at the Urban Farm Fermentory in Portland, Maine

More places for beer tastings in Maine where you can take the kids.

Working off the calories

The natives have no problem with playing outdoors in winter. In fact, they celebrate it with the Great Maine Outdoor Weekend in mid-February, right in the thick of the coldest season. We spent some of the calories we ingested at all the places listed above with some outdoor and indoor activities.

Willard Beach, Portland, Maine in WinterWillard Beach is a sweet beach on a quiet bay in South Portland, with a playground right on the beach. There is a public parking lot on Willow Street. You absolutely must stop by Scratch Bakery for the best, chewiest, bagels on earth. No joke. Note that Willard Beach is open to off-leash dogs in the morning and evenings in summer and all day in winter, which might be a plus or a minus for you.

Candlepin bowling in winter in Portland, Maine.

Candlepin Bowling is unique to New England and Eastern Canada, and a perfect activity for families that include younger children. The balls are small and lightweight, and the pins are, too. And you can still ask for bumpers. Big 20 Bowling Center  is located at 382 U.S. Rte. 1 in Scarborough, just a 20-minute drive from downtown Portland. Bumper bowling is $20 per hour. Regular games are $3.25 per game.

Impromptu outdoor hockey scrimmage in Portland.Outdoor ice-skating was a surprise for us, mostly because it was not a manicured rink, but simply a flooded and frozen field in a local park. We borrowed ice skates and hockey sticks from our hosts and spent a glorious hour pretending to be Olympians. If you don’t have a local source, a new resource in Portland is the Portland Gear Hub, which lends out equipment to members. An $80 family membership might be steep for a weekend, but it might also be worth it for the fun you’ll have. Payson Park on Baxter Boulevard, where we skated, also has a hill for sledding, snowboarding and even skiing.

So what’s the secret to surviving a winter weekend in Portland? Just go and do what the Portlanders do: eat, drink, and be merry, without the summer crowds!

If you’re traveling to Maine with kids in summer, check out this article on things to do in Maine with kids from a local mom.

Click here for more things to do and places to stay in Portland.