Portland in 48 Hours

Portland is a thriving, energetic, and innovative city, where residents work hard and play hard. It has diverse neighborhoods, from the historic Old Port and East and West Ends on the peninsula to the more suburban neighborhoods off the peninsula. All over the state’s largest city you’ll find unique, locally owned restaurants, pubs, markets, and shops.


3:00 p.m. @ Shift 

I’m kicking off what will surely be a food-filled weekend with a good workout. At Shift, owners Tom Kropf and Rebecca Woll push racks of fashionable fitness gear to the side and train clients at the fitness studio and retail shop. My weekend is off to an energizing start.

4:00 p.m. @ The Press Hotel

The lobby is tastefully decorated for the holiday season, and I’m greeted warmly the moment I arrive. While I expected a chic and comfortable room, I am surprised, and delighted, to find a corner suite complete with a kitchenette, living room, two bathrooms, fireplace, and even a private roof deck.

4:30 p.m. @ Vena’s Fizz House

This is my first visit to this bar and shop that sells a wide array of barware, mixers, and ingredients. I meet up with a friend over a warming Spiced Pear Sidecar with brandy and cardamom-clove syrup for me, and a Dim and Stormy, one of Vena’s non-alcoholic mocktails, for her. We chat with chef Stephanie Shershow, who tells us that everything on the menu uses bitters. There are several vegan options and lots of small bites, created to complement the drinks.

6:00 p.m. @ The Inkwell

Back at the Press Hotel, I meet photographer Nicole Wolf for a glass of prosecco at the Inkwell bar in a corner of the lobby. She and I work together a lot but rarely have time to socialize, so this is a great place to catch up. With the bitter temperature outside, our spot by the fireplace is very inviting. The lobby is bustling with guests taking refuge from the cold and enjoying the pervasive holiday spirit.

8:00 p.m. @ Sur Lie

My husband, Bob, and I brave the cold for the short walk to Sur Lie, a tapas-style restaurant on Free Street. Sharing a series of small plates by the talented chef Emil Rivera lets us enjoy a variety of tastes. We agree that the scallops on white sweet potato puree is our favorite and finish our meal with a decadent apple cider doughnut topped with gelato and maple syrup.


8:00 a.m. @ Union

We pull aside the curtains and discover that it’s snowing heavily. No matter; we can do all our shopping and dining on foot today. A hearty breakfast of thick French toast and berries at the hotel’s restaurant, Union, fortifies us for the day ahead.

10:30 a.m. in the Old Port 

Bundled up, I head down Exchange Street in hopes of completing my Christmas shopping. My first stop is Abacus, for the whimsical art and crafts, elegant jewelry, and one-of-a-kind gifts. Just a few doors down is Fat Face, a British import that sells casual clothing, where I find a pair of super-soft sweatpants for my younger daughter. My oldest, Lara, works nearby at Judith, a chic boutique filled with carefully curated women’s clothing and accessories. I pick out some silver earrings—she can suggest to my husband that I might like to find them under the tree.

12:30 p.m. @ Fork Food Lab

This community kitchen and food incubator in Bayside is holding a holiday open house. The Marshmallow Cart is by the door, serving up s’mores in the snow. Indoors, an enthusiastic crowd is exploring the big commercial kitchen while members offer tastings of their products. White Cap Coffee has nitro cold brew that goes well with the baked treats from Fat Pants Bakery and Chalkboard Baking. Co-owner Eric Holstein is serving hot chocolate and mulled wine in the tasting room.

2:00 p.m. @ Liquid Riot Bottling Company

We head back to the Old Port for a light lunch at Liquid Riot on the waterfront. It’s an expansive brewery, distillery, and resto- bar with an eclectic menu of upscale bar snacks, sliders, and sweets. Beer cheddar popcorn and a house-made pretzel with spicy mustard hit the spot with a blond Kash Money IPA, brewed on the premises.

3:00 p.m. in the Old Port 

Shopping for stocking stuffers brings me to Motifs (funny socks) and LeRoux Kitchen (spices, kitchen gadgets). At Uncommon Paws, a new shop for pet accessories on Exchange Street, I meet owner Gudrun Cobb, who helps me pick out a few items for my dog, Cricket. In Monument Square, I can count on Longfellow Books for an excellent selection, including new cookbooks and a copy of The Hitchhiker’s Guide to the Galaxy to give as a gift.

5:30 p.m. @ Union

The bar inside Union overlooks the big, open kitchen and it’s fun to watch chef Josh Berry and his crew preparing dinner. Bartender Sarah Graff mixes me a cocktail, called the Down East, a tasty blend of spiced pear liqueur, bubbles, and lemon. The atmosphere is convivial, and Union’s staff really seems to enjoy chatting with guests.

6:30 p.m. @ Woodford Food and Beverage

We meet up with my sister and brother-in-law for dinner at this lively spot off the peninsula. Owners Birch Shambaugh and Fayth Preyer renovated the space in a cool midcentury style with a handsome bar. Open for about a year, it’s developed a reputation for friendly service and a menu that blends American diner and French brasserie fare. We dine on stuffed clams, fantastic Brussels sprouts, burgers, and mussels and frites, expertly prepared by chef Courtney Loreg.

8:00 p.m. @ The State Theatre

We’re just in time for the Fogcutters Super Fantastic Christmas Extravaganza, featuring the 19-piece big band the Fogcutters, along with some of Portland’s best local musicians. Holiday classics are performed with flair by Anna Lombard, rapper Spose, Maine bluegrass pioneer Al Hawkes, and Maine magazine’s own Spencer Albee. Upon our return to the Press Hotel, we run into the hotel’s developer, Jim Brady, and his family. They have just attended the Portland Symphony Orchestra’s Magic of Christmas.


9:00 a.m. @ Quest Cycle

The snow has turned to rain, and it’s a messy day. I’m so tempted to stay in the luxurious bed and order up coffee, but I’ve signed up for a spinning class at Quest on Marginal Way. The instructor makes us sweat it out for an hour, while scenery projected on the wall lets us pretend we’re in sunny Tuscany. It’s a terrific workout, and I have definitely earned brunch.

11:00 a.m. in the West End

Caiola’s, an old favorite in the West End, is now owned by Damien Sansonetti and Ilma Lopez of Piccolo, who have plans to renovate the restaurant. I need to refuel after all that exercise, and the confit duck and mushroom hash with eggs is delicious. Afterwards, I make a stop next door at Aurora Provisions, a neighborhood cafe and market with a large selection of prepared foods, wine, chocolate, and gourmet gifts. I choose some beautifully decorated holiday cookies to take to friends later on.

1:00 p.m. @ Reny’s

At Reny’s, our last stop before heading home, I’m happy to find several things I had forgotten I need, including wrapping paper. Bob chooses something fun for his office Yankee swap and browses the Carhartt section for cold weather gear. I’ve loved spending the weekend in Portland, walking almost everywhere we want to go. This taste of city life has me dreaming of a day we could live here, taking advantage of all it offers every day.