Seasonal Weekend Excursions

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Exploring the region via short escapes to recharge

In our busy lives, it’s often hard to find the time to get away for long vacations. Luckily, we live in a region filled with amazing sites, diverse natural beauty, and a myriad of culinary delights. You can reach the beach or the mountains in a couple of hours and feel like you are in a completely different world. Here are some spots—some perhaps, lesser known to most—to explore for a short break if you just need a fun, interesting escape.

Frederick, Maryland

For history, shopping, and delicious dining options, Frederick is a perfect day trip or weekend getaway less than an hour and a half away from our state capital Annapolis. Start your excursion at the National Museum of Civil War Medicine. This interactive museum gives you a glimpse into the techniques used during a brutal period in history while highlighting the courage of the participants. The methods used during this period laid the foundation for modern medical care. It’s a fascinating experience that you will remember forever. Once you’ve had your fill of the museum, take a leisurely stroll around downtown and enjoy all of the adorable boutiques, antique stores, bookshops, and restaurants. Walk along Carroll Creek Park and appreciate the beautiful views of the creek that winds through the heart of downtown. Make sure to visit the Claire McCardell Statue, commemorating her important legacy in the fashion industry.  The town is filled with quaint breweries and distilleries, and you won’t want to miss sampling Idiom Brewing Co., Attaboy Beer, and Steinhardt Brewing Company. Frederick has turned outdoor dining into an art form and some great options include The Orchard, Truth and Beauty, and the Wine Kitchen. If you want to stay overnight, you can enjoy gorgeous B&Bs such as 10 Clarke Bed and Breakfast or the Hollerstown Hill Bed & Breakfast, both a short walk to the shops and restaurants. After a weekend in town, you will feel relaxed and rejuvenated.

Boonsboro, Maryland

For outdoor enthusiasts and book lovers, consider a getaway to Boonsboro. Located about an hour and a half to the northwest of Annapolis, the Appalachian Trail winds right through town. You can tour the Crystal Grottoes Cavern, which has been wowing tourists for over 100 years, or spend a day at Greenbrier State Park, walking and biking the trails, or swimming in the freshwater lake. In nearby Devil’s Backbone Park, you can fish or rent a canoe or tube for the creek, along with investigating more gorgeous trails through the beautiful forests. Back in town, take an afternoon to browse Turn the Page Bookstore, owned and operated by Bruce Wilder, husband of bestselling author, Nora Roberts (additionally writing as J.D. Robb). The store often holds literary events and features a wide array of signed copies by Roberts. Nearby, you can stay at the Inn Boonsboro on the Square, also owned by Wilder and Roberts. Each adorable room is themed after famous literary couples like Elizabeth and Darcy from Pride and Prejudice, or Jane and Rochester from Jane Eyre. Enjoy dining at The Branded Chophouse or The Yellow House for casual food and great cocktails.

Thurmont, Maryland

For gorgeous wineries and stunning orchards, look no further than a jaunt to Thurmont. In under two hours from Annapolis, you will be surrounded by breathtaking scenery. You can hike and camp in Cunningham Falls State Park or the adjacent Catoctin Park and enjoy epic, sweeping views of the surrounding landscape. Visit the Catoctin Wildlife Preserve and get up close and personal with hundreds of exotic animals in a lush, 50-acre park. You can even take a one-hour safari ride showcasing animals from six continents. Come fall, visit Catoctin Mountain Orchard to pick your own fruit, enjoy homemade baked goods, and purchase jams, produce, and gifts. When you are ready for a glass of wine, stop in the Catoctin Breeze Vineyard & Winery, where you can savor tastings while you admire the sunset. You could spend a day driving around to an assortment of other orchards and wineries, as well. As you head to dinner, be on the lookout for one of the delightful, covered bridges around town. For dining, don’t miss out on Thurmont Kountry Kitchen, Bollinger’s Restaurant and Uncle Dirty’s Brew Works, or 10Tavern. Stay nearby at Antrim 1844 in Taneytown, a 24-acre estate renowned for its upscale accommodations. 

Harper’s Ferry, West Virginia

Hikers and nature buffs will definitely want to make the trek to Harper’s Ferry. You will drive less than two hours from Annapolis and feel like you are in another world. The Appalachian Trail Conservancy Headquarters resides in town and is one of the most famous landmarks of the 2,190-mile trail. It is often considered the psychological halfway point for hikers who traverse the whole trail. For those of you who might not have the six months to hike the whole Appalachian Trail, spend time exploring the Harper’s Ferry National Historic Park. You have nearly unlimited trails to discover, along with major historic sites and cute shops to browse. For a scenic overlook that will take your breath away, hike up to Jefferson Rock. For kids, and kids at heart, stop at the Joy Line Railroad and Toy Train Museum. For dining, try the Rabbit Hole Gastropub or Kelley Farm Kitchen and enjoy some libations at The Barn. There are plenty of B&Bs for overnight accommodation. Check out The Town’s Inn, Light Horse Inn, or the Angler’s Inn. When spring blooms there are few places more beautiful than Harper’s Ferry.

Confluence, Pennsylvania

About three and a half hours away, Confluence is the perfect spot for anglers and architecture enthusiasts. In Ohiopyle State Park, enjoy a day of fishing in well-stocked rivers and streams, or wander through almost 80 miles of trails. For adventurers, Mount Davis is nearby, beckoning hikers to summit the highest peak in Pennsylvania. For those ready to experience legendary architecture, take a tour of Frank Lloyd Wright’s Fallingwater (pictured). Prepare to be amazed by this timeless structure that marries nature and architecture in a stunning setting. You can walk the grounds, as well as peruse the inside of the house.  For dining, visitors and locals love the Lucky Dog Café, Mitch’s Fuel & Food Restaurant, and the River’s Edge Café. Accommodations run from rustic charm to relaxed B&Bs. Two standouts are the Paddler’s Lane Retreat and the Smith House Inn. There is also an array of cabins to rent in the area. For a more upscale stay, check into the Nemacolin Woodlands Resort for a 5-star stay and access to sporting clays, fly fishing, and other year-round onsite recreation.

Middleburg, Virginia

If horses and wineries pique your interest, head to Middleburg, less than two hours away from Annapolis. Middleburg is known as America’s horse and hunt country capital. Learn all about this accolade at the National Sporting Library & Museum, featuring artifacts and fine art illustrating the rich history of sporting life, including steeplechasing, foxhunting, polo, horsemanship, wildlife, and more. Once you have finished at the museum, start your wine tour. You will enjoy visits to Boxwood Estate Winery, Greenhill Winery and Vineyards, and 50 West Vineyards. There are many more if you want to make a full weekend out of wine tasting. If wine isn’t your thing, but you still want to enjoy the views, the family-owned Lost Barrel Brewing might be just the ticket.  Stay and eat at the Red Fox Inn and Tavern, or the Salamander Middleburg. Both have been around a long time and are quite famous in the area, offering fantastic guest experiences and rooms. Other great dining options include Tremolo Bar, Red Horse Tavern, and the King Street Oyster Bar. Middleburg offers so many opportunities to sit outside, sip on something delicious, appreciate farm-to-table treats, and take in the serene views. 

Cape May, New Jersey

Before beach season ramps up, visiting the shore has a different, and arguably, magical vibe with fewer crowds and just as much opportunity. If you enjoy lighthouses, birding, and peaceful moments at the beach, consider a jaunt to Cape May. You can have a truly relaxing getaway in around three and a half hours from Annapolis. In addition to resting on Cape May Beach, pay a visit to the Naval Air Station Wildwood Aviation Museum and marvel at the vintage aircraft collection. You may prefer to mingle with Alpacas at Jersey Shore Alpacas. Or perhaps you would like to take a nice stroll down the Washington Street Mall, the historic shopping district for pedestrians. For birdwatchers, the Cape May Bird Observatory is a spectacular location to spot them. National Geographic has listed Cape May as a “World’s Best Destination” for birding. Cap off a visit to Cape May with a tour of the Cape May Lighthouse. For fine dining try Grana BYOB or the Washington Inn. For more casual fare, give Mario’s Pizza & Italian Eatery a shot. You have a lot of options for accommodations, but a couple of standouts are Angel of the Sea, the Bedford Inn, or the Carroll Villa Hotel.  You don’t have to go too far to have a short, but sweet, getaway. A visit to any one of these spots will create lasting memories. They all deserve a spot on your bucket list.