1. Running With Santa
During the holidays, the boardwalk in Virginia Beach glows with coastal-inspired light displays—pirate ships, dancing seahorses, open-jawed sharks. A fun way to see it is to run the Surf-n-Santa 5 Miler at twilight on December 20. While there, make a weekend of it. You can join naturalists from the Virginia Aquarium & Marine Science Center on a whale-watching trip—winter is when migrating humpbacks trace the coastline. This also happens to be the time of year that horseback riding is permitted on the beach; you can saddle up with Virginia Beach Horseback. Cold weather means oyster season, too, so consider a tour and tasting at Pleasure House Oysters. You can book an oceanfront room at the new Hilton Garden Inn on the boardwalk; it offers a stylish indoor pool and local beer on tap at the buzzy bar. Rooms from $129.
2. A Very Cool Place
Downtown Pittsburgh is transformed into a winter wonderland each year with the outdoor ice rink at PPG Place and a German-style Christkindlmarkt, where international vendors sell handicrafts from wooden chalets. The Duquesne Incline, an uphill cable car that overlooks the city, is lit with hundreds of red lights. And this is a great city for quirky, with events such as the Dirty Dozen (an icy uphill bike race) and, in the hipster neighborhood of Lawrenceville, the Joy of Cookies tour. You can also admire Gilded Age holiday finery at Clayton, the former mansion of industrialist and art collector Henry Clay Frick. Stay at the sleek new Fairmont hotel, which has a resident dog named Edie (as in Sedgwick—this is Warhol’s hometown, after all). Rooms from $259.
3. Take the Plunge
They call the snowtubing park at Virginia’s Wintergreen Resort simply the Plunge—and plunge you will, at speeds up to 30 mph down a hillside with a vertical drop equivalent to that of a ten-story building. With ten lanes running the length of three football fields, it’s the largest snowtubing park in the state. (Ninety-minute sessions are $26 on weekends, $18 weekdays.) For little tubers under 42 inches tall—the height required to take the plunge—there’s Ridgely’s Fun Park with its mini-tubing carousel, bear-paw snowshoes, and a much smaller plunge. $18 for one adult and child, $10 extra per child and $5 extra per adult. Wintergreen has a variety of overnight options, from hotel-like guest rooms ($155 and up) to apartment condominiums ($175 and up) to house rentals ($289 and up).
4. Winter in Williamsburg
The Grand Illumination kicks off the holidays at Colonial Williamsburg. Fireworks blaze over the historic village on December 7, and period homes throw open their doors to showcase holiday decorations through January 4. Meanwhile, the Spa of Colonial Williamsburg, an airy retreat with aromatherapy steam baths, features treatments that take aim at moisture-deprived winter skin. Stay in one of the new cottages fronting the James River, each tricked out with fireplaces and stylish kitchens, at Kingsmill Resort, which runs a free shuttle to the Revolutionary City. Rooms from $149, three-bedroom cottages from $699.
5. Mansions and Microbrews
In the Brandywine Valley of Pennsylvania and Delaware, beautiful holiday decorations deck the halls at the DuPont family mansions—Winterthur, Nemours, and Hagley, the original homestead—while acres of winter plantings, fountains, and candlelit treehouses tempt at Longwood Gardens. The swank life doesn’t have to end when the mansion tour does: You can dine in front of the fireplaces at the historic Dilworthtown Inn and stay in an 18th-century man-or house at Sweetwater Farm, an estate on 50 acres that’s owned by the late Princess Grace’s nephew. Rooms and cottages from $150. On February 28, Winterfest takes over the town of Kennett Square, Pennsylvania—“the mushroom capital of the world”—with local bites, beers from 40 craft brewers, and live music.
6. Bounty of the Bay
Winter means one thing to many on the Eastern Shore of Maryland: oysters. Harrison House Charter Fishing, owned by the same Tilghman Island family for generations, takes visitors on oyster-dredging outings on a skipjack. Or just eat the bivalves: Back at Harrison’s Chesapeake House, the Friday-night buffet includes oysters Rockefeller, fried oysters, and oysters on the half shell. Stay overnight at the nearby Tilghman Island Inn. The rooms have broad water views, and the restaurant, reimagined under new ownership, serves fresh local seafood like—naturally—oysters. Rooms from $175.
7. Snow Fun
The prime location of Massanutten Resort in Virginia’s Shenandoah Valley means it’s tailor-made for winter pleasures such as skiing, snowboarding, tubing, and ice skating. When you’re ready for warmer fun, you’ll find an elaborate indoor water park, a family-friendly spa experience, crafting classes with grown-up offerings like digital photography, and a new healthy-living program in which guests can take healing-herb workshops and tai chi classes. A crisp winter night demands a window seat at Fareways, the resort’s laid-back restaurant, where you can order a flight of Virginia wine and watch the lights from the ski run twinkle in the Blue Ridge Mountains. Rooms from $150.
8. Wine and Dine
Throughout the year, the Peacock Restaurant & Lounge at the Inn at 202 Dover in Easton, Maryland—which Food & Wine named one of the best bed-and-breakfasts in America—celebrates the grape. On February 27, the restaurant hosts an Italian-wine dinner featuring small wineries, such as the Rocca di Fabbri Estate in Umbria run by sisters Roberta and Simona Vitali. The chef, who has cooked at the prestigious James Beard House in New York, will pair the wines with a five-course Italian-accented dinner. You can hunker down at the inn with your honey for the weekend in one of the plush suites, the smallest of which is 600 square feet. The wine dinner costs $100 a person, but if you also book an overnight room—rates start at $475—the dinner drops to $75 a person. Book two nights and the second night is half price.
9. Winter Wildlife
Late February through early March is the peak time of year to witness the annual snow-goose migration, where as many as 80,000 birds create a blanket of white in the sky over northern Lancaster County, Pennsylvania. Also in February, check out local food, microbrews, and music at the Fire & Ice Festival in Lititz, dubbed the coolest small town in America by Budget Travel magazine. Stay at the Speedwell Forge B&B, an 18th-century stone mansion that’s home to the Wolf Sanctuary of PA, where you can take a full-moon tour and get up close to the 46 rescued wolves in residence. Rooms from $135, cottages from $250.
10. Your Best Foot Forward
The folks at Savage River Lodge in Frostburg, Maryland, say that if you can walk, you can snowshoe, which means you won’t need snowshoeing lessons if you’ve never tried the sport. The lodge offers rentals of snowshoes ($25 a day) and cross-country skis ($35 a day) for exploring the property’s 14 miles of wooded trails. The best part: After your walk in the woods, you can relax with a gourmet meal and a massage by the fire in your own private cabin. Standard queen cabins start at $225.
11. Cooking in the Country
Hole up in an antiques-decorated room in the mansion or gather a group in the Carriage House at the Clifton Inn, a Relais & Châteaux property outside Charlottesville, Virginia. Chef Tucker Yoder, a farm-to-table devotee, cooks fabulous meals, often with ingredients from the inn’s garden. Learn how to make holiday hors d’oeuvres and cocktails this month during “12 Days of Clifton,” a hands-on cooking-demonstration series at the marble-topped counter in Yoder’s intimate kitchen. Classes run from December 13 through 24 and cost $20 to $35 a person. After the new year, classes, demos, and tastings feature winter’s bounty. Rooms from $199, cottages from $279.
12. Going Cross-Country
About three hours west of DC, White Grass in Davis, West Virginia,is a touch of Scandinavia on the East Coast. It boasts some of the area’s oldest and most extensive Nordic cross-country ski trails, with more than 30 miles of manicured, wooded routes, plus full ski rentals and lessons for newbies ($15 per hourlong lesson). Its laid-back White Grass Cafe serves up tasty organic cuisine and live music on weekends. After a day on the trails, bunk among the funky furnishings at the nearby Cooper House Bed & Cocktail. You’ll have to scout your own breakfast in town, but innkeeper Joy Malinowski provides the hors d’oeuvres—and makes a mean martini. Rooms from $90.
13. Flex Time
No snow? No worries. Head to Liberty Mountain’s Snowflex Centre in Lynchburg, Virginia, the country’s first artificial-snow park. Snowflex is a synthetic material that simulates the feel of the real thing—without the chill—so skiers, snowboarders, and tubers can hit the slopes year-round. The park includes beginner, intermediate, and advanced slopes plus an 11-foot-tall quarter pipe, a wall ride, and a 90-foot-long landing ramp for snowboarders and skiers. An alpine-like day lodge lets you warm up inside—or cool off as the case may be. For overnight accommodations, head to the boutique Craddock Terry Hotel, in a renovated shoe factory in Lynchburg’s historic district. Rooms from $149.
14. Hanging With the Peeps
Bethlehem, Pennsylvania, is home to the Just Born factory, which produces some 5 million Peeps every day. So it’s no surprise the marshmallow confections are the theme of an annual Peepsfest, December 30 and 31. Live music, an African penguin, a dogsled team, arts and crafts, and a Peeps scavenger hunt are some of the activities, most of which are free. The highlight, though, is the New Year’s Eve drop of a 4½-foot-tall, 85-pound, brightly lit fiberglass-resin Peeps at 5:15 pm (early enough for children to enjoy), followed by fireworks. Known as the Christmas City, Bethlehem also offers horse-drawn carriage rides and other city tours. The Historic Hotel Bethlehem puts you within an easy walk to restaurants, boutiques, and the Moravian Book Shop, the oldest continuously running bookstore in the world (established 1745).
This article appears in the December 2014 issue of Washingtonian.