It's never really a bad time to visit Baltimore. This is, after all, one of the country's oldest and most unique cities, a place of incredible history, culture and architecture. Unlike so many other stops along the Northeast Corridor these days, Baltimore remains a haven for creative types, a place that celebrates oddity, quietly delights in its own quirkiness and knows better than most how to balance work and play. The food is great, there's always plenty to drink and – perhaps best of all – the locals can be some of the friendliest you'll find in an American city. While the weather outside may be growing more frightful by the day, indoors, already-cozy Baltimore amps up that pre-existing warmth and charm in the run-up to the holiday season, making this one of the secretly-best cities in which to disappear and relax for a couple of December days.
Stay: One of the most promising new small hotels in the country opened in the heart of Baltimore last year – the soon-to-be-a-classic Ivy Hotel brought even more charm and style to an appealing corner of Mount Vernon, a grand, largely residential neighborhood just above Baltimore's downtown. Hiding in plain sight, the hotel has less than twenty rooms, with abundant and lavishly decorated common areas (both in and out of doors) available exclusively to guests. Hotel hounds will not be surprised to learn that the Ivy is a member of Relais & Chateaux, a consortium of some of the world's best small hotels and restaurants. Want to do it up but prefer to be right on the city's famed Inner Harbor? The next big luxury hotel opening will soon happen on the Fells Point neighborhood's historic Broadway Pier, but that's still a few months off – for now, you'll have to settle (oh, darn) for the superb Four Seasons, practically hanging over the water in the modern Harbor East district. A Vegas-worthy Sunday brunch buffet and one of the best urban hotel spas on the East Coast make the hotel a must on a civilized Baltimore weekend, whether you spend the night or not. Looking to keep lodging costs down? Besides the two aforementioned, hotels in Baltimore are nearly always quite affordable, with a laid-back but typically friendly service culture making just about anywhere you stay a reasonably pleasant experience. To really relax without breaking the bank, check in to the Radisson Cross Keys, a classic, resort-like property up in the trees, just a short drive (or Uber ride) from the harbor. The hotel is tucked inside one of the country's first modern mixed-use developments (Oprah lived here!), just next door to the understated grandeur of the adjacent Roland Park neighborhood, which will have you opening your favorite real estate app (and, no doubt, have your eyes bulging out of your head when you see those low, low prices).
See: December weather gives visitors the perfect excuse they need to disappear into Baltimore's excellent museums. For most people, the American Visionary Art Museum should be the first stop – dealing primarily in what's known as "outsider art," there's so much here you'll probably not have seen before. Need to do some last minute gift shopping? Here you'll find one of the most unusual museum shops of all time. From here, you're just a short walk to the nearest stop of the free Charm City Circulator bus service, specifically the route that can take you to the Baltimore Museum of Art and Walters Art Museum. Both are world-class institutions that offer continuous free admission. Feeling festive? There are plenty of seasonal events around town, from the harbor-front Christmas Village, a proper German-style holiday market (there's a skating rink nearby, if you're in the mood) to the famous Miracle on 34th Street light show on one brilliant block in the Hampden neighborhood, another great place for one-of-a-kind Christmas gift shopping, by the way, since you're up there. Far off the beaten path, but equally worthy, is the annual Christmas Cookie Tour, a festive open house that brings in-the-know locals out to the old Union Square neighborhood, a beautiful relic of Baltimore past and one-time home to H.L. Mencken (Dec. 11, tickets at union-square.us). Finally, while it's always a good idea to drop in on the B&O Railroad Museum – housed at, quite literally, the birthplace of American rail travel – its Magical Holiday Express celebration features themed events and train rides with everyone from Frosty to Santa to Elsa and Anna (yes, that Elsa and Anna). Finally, speaking of characters, if you're here on December 21, the only place you should be at 8pm is the Baltimore Soundstage for the annual John Waters Christmas show, a one-man festival of oddities that is just about the most Baltimore way you could ever celebrate the season. It sells out fast.
Eat & Drink: With too many markets and food halls, new and old, to sample from during one visit, Baltimore is pretty much heaven for people who really like to eat. Start with cheap and good oysters everywhere, move on to classic crab cakes at Faidley's in the ancient, blue collar Lexington Market, then choose from smoked fish sandwiches, spicy ramen and housemade kombuchas or anything else that sounds good at the cool but not-too-cool Belvedere Square Market, another gem far off the tourist trail. Oh, and don't forget Mount Vernon's newish Marketplace food hall, adjacent to a sleek, all-day café from Maryland's best roaster, Ceremony Coffee. To hang with the coolest crowd in town, you'll want to look to the largely fallow (but up-and-coming) blocks west of Howard Street, just north of Penn Station – here, the sleek new R. House residential development will include a food hall of its own, while mostly-locals-only, secretive spots like the W. C. Harlan cocktail bar and their newer, top-notch mezcal bar (with queso and tacos, because obviously), Bar Clavel, are essentially Baltimore musts at this point. Of course, the same goes for the restaurants helmed by recent James Beard Award-winner Spike Gjerde – the formidable Woodberry Kitchen, a celebration of Mid-Atlantic food and culture, is now almost old school but no less important than the day it opened, particularly during dinner. Don't miss, however, the chance to at least look in on his newer joints, including the marvelously meat-centric Parts & Labor and the Johns Hopkins-adjacent Bird in Hand bookstore café, opened in partnership with a local bookseller. Stuck on the Inner Harbor? Book a table at Charleston, for years considered Baltimore's best restaurant for good reason. Elegant interpretations of Lowcountry cuisine coupled with wonderful Baltimore service, white tablecloths and one hell of a cheese cart make this one of the most memorable classic nights out anywhere – one that feels as essential now as it did back when this is what all fine dining looked like.