The holiday season is racing by, and many of us are in a frenzy of final preparations. Whether you’re looking for a day of fun as things slow down between Christmas and New Year’s, or you’re looking for something to put on your calendar in the bleak post-holiday months of January and February, there are special experiences waiting for you all over the Chesapeake Bay.
At Chesapeake Bay Magazine, one of our favorite activities is to brainstorm fun day trips or overnight stays in the Bay region’s many waterfront towns. We hope that sharing our staff’s mini-trips will inspire you to hop in the car and expand your horizons close to home this winter.
Couples’ Retreat on Tilghman Island, Creative Director Jill Allen
I’m gifting my husband a night at the Wylder Hotel Tilghman Island for Christmas over winter break. We’ve been in the summer and had the best time. I’m looking forward to visiting in the winter for the fire pits and boozy hot cocoa bar!
Tilghman is the perfect place for us to reconnect, sans kids. Wylder has cute bikes you can use to get around the island which is the perfect way to explore. The quiet location gives you a chance to unwind, and there are so many good spots nearby I’m looking forward to visiting.
While we’re in Talbot County, we’re definitely going to spend a day in St. Michaels. I want to check out Eastern Shore Brewing and then do some post-Christmas shopping downtown. Antiques on Talbot is one of my favorite shops and we both love visiting the Chesapeake Bay Maritime Museum.
Old-Fashioned Winter in Yorktown & Williamsburg, Executive Vice President Tara Davis
Yorktown, Virginia, is a fantastic nearby getaway for anyone along the Chesapeake Bay, with a mix of history, natural beauty, and modern attractions. My family and I always enjoy this trip—it was great when my kids were younger, and now that they are teens, they still enjoy it.
This charming town has cafes, shopping and waterfront views. For a real taste of 17th- and 18th-century celebrations, Christmastide in Virginia runs through New Year’s Eve in Jamestown and Yorktown.
Just a short drive away, Colonial Williamsburg and Busch Gardens offer even more fun, from living history exhibits to amusement park rides for all ages. We usually make Busch Gardens Christmas town a “must visit” on our holiday to-do list. My two girls have been enjoying it since they were 4 and 6.
Family Fun in Cambridge, Editorial Director Meg Walburn Viviano
With two elementary school-aged children on winter break, my family is going to stretch the holiday magic as far as we can. Cambridge, in Dorchester County, is the perfect distance from our house for a quick trip. It boasts a crab basket Christmas tree and the longest continually operating fire department train display in the United States. Running since 1934, the iconic Rescue Fire Department Train Garden (open through New Year’s Eve) is sure to be a hit with my boys.
My family enjoys the Hyatt Chesapeake Bay Resort in Cambridge year round, but we’re especially excited for the low off-season rates and the new, cold-weather activities. This winter they’ve installed a synthetic ice-skating rink, operating throughout the winter. The nearby Winter Village includes a hot chocolate station, cocktail bar, and fire pits for roasting s’mores. The resort’s glass-enclosed “Winter Garden” has a 23-meter heated pool we love, indoor/outdoor hot tub, and a schedule of nightly “dive-in” movie screenings.
Festive Historic Annapolis Pub Crawl, Eileen Rodgers, Digital Content Manager
Annapolis is magical over the holidays, adorned in holiday decorations, trees, garlands, snowflakes, bows and lights, perfect for an annual self-guided Christmas Crawl. My family usually switches it up, but this year we’ll start on Main Street at the Red, Red, Jingle Bell Bar where ‘wine on tap’ and an Elfie Station awaits.
Then we’ll walk up the hill to Church Circle and find ourselves in Christmas Past at the 1747 Pub below Reynold’s Tavern with its original stone and brick walls, walk-in fireplace, low ceilings and brick floors. From there, we will wander over to a modern-day speakeasy below Aqua al 2. If you haven’t, it’s a must. We’ll continue to Harry Browne’s on State Circle and take the narrow staircase to the upstairs bar and chill out on the large comfy leather chairs.
We will end the evening with a nightcap at Galway Bay, a family favorite on Maryland Ave, which is one of the prettiest streets downtown. Galway Bay is a true public house offering real Irish hospitality and incredible eggnog, which mixes perfectly with every one of their fine spirits. As always, it will be a night to remember, good times with the family in a special place.
Northern Neck, Editor-at-Large John Page Williams
When my wife and I are looking for a place to spend a long winter weekend with a mild forecast, we’d head to Virginia’s Northern Neck. Lying between the lower Potomac and Rappahannock Rivers, it has played prominent roles in America’s history for centuries, including birthing Presidents George Washington, James Monroe, and James Madison.
At Christmastime, the area lights up with decorations and special events. We’d start by walking around Montross, the Westmoreland County Seat, a lively arts center highlighted by locally themed murals. We’d look for an attractive B&B and visit several nearby attractions (it’s too hard to choose one or two!): George Washington’s Birthplace National Monument, the Lee Family’s Stratford Hall, and Westmoreland State Park along the Potomac. On the Rappahannock, we’d look for bald eagles and waterfowl as we walked the trails of The Nature Conservancy’s Voorhees Nature Preserve and stop by the public landing at Carter’s Wharf, in the middle of the river’s spectacular Fones Cliffs.
Finally, we’d visit at least one of the region’s wineries, starting with Ingleside Vineyards, and look for an event involving our friends at the local farm-to-table caterer, Denson’s Grocery, in business since 1912.
Toasty Tastings in Cape Charles, CEO John Martino
Cape Charles, Virginia, offers a serene and peaceful winter getaway. I could use an escape from the hustle and bustle of this season. While it’s well-known as a summer vacation destination due to its beautiful beaches and vibrant atmosphere, winter brings a quiet charm to this beach town at the mouth of the Chesapeake Bay.
With slightly milder winter weather than the upper Chesapeake Bay, Cape Charles is perfect for leisurely winter walks along the beach or exploring the town’s quaint streets. The historic architecture, cozy inns, and locally-owned restaurants provide a warm, welcoming vibe even in the colder months. We love the Cape Charles Distillery, where the local spirits warm you up and Virginia oysters are in season.
Cape Charles in winter is a refreshing retreat from the holiday season.
