After the couple of years we’ve had, the restlessness is real — and so are the mounting concerns that we might be in for another cooped-up winter. But luckily, while fresh air and gorgeous fall temps remain, we still have the freedom to get outside and enjoy every bit of fun our diverse region has to offer. Here are a half-dozen hidden gems to visit this fall and our suggestions on how best to enjoy them.
St. Michaels, Maryland for a Girlfriend Getaway
The Gist: This charming hamlet features all the girlfriend getaway-bait you could ever dream up: quaint shops, quality restaurants, water views and a winery.
Where to Stay: The Inn at Perry Cabin (fall rates run $530-$1,200 per night) is a classic and a worthwhile splurge (plus, you can brag about staying where “Wedding Crashers” was filmed), but there’s a new kid in town. The Wildset (fall rates run $139-$479 per night) brings a cozy yet modern aesthetic to the historic town, along with more reasonable rates and thoughtful touches like books, paintings and photographs.
Where to Eat: Try the brand-new Ruse located in the Wildset, which pulls heavily from coastal cuisines from around the globe and is a nod to a trick the town played on the British during the War of 1812. Or, go with some tried-and-true options like Ava’s Pizzeria and Wine Bar to hone your ladies who lunch vibe. Other tasty options include The Crab Claw for the quintessential Eastern Shore crab shack experience; the well-regarded 208 Talbot for chef David Clarke’s upscale American dishes; or the chef’s tasting menu at Stars, the dining room at the Inn at Perry Cabin.
What to Do: Take a break from shopping and eating with a spa treatment at Perry Cabin. Later, sip some wine at St. Michaels Winery, conveniently located on the town’s main drag (Talbot Street) so nobody is stuck with designated driver duties. And since you’re right on the water, learn more about the bay with a visit to the Chesapeake Bay Maritime Museum. Better yet, get on the water with an hour-long Miles River tour.
Hideaway Co. for Maryland Glamping
The Gist: Hideaway Co., founded by one of the folks who launched Ace Hotel Pittsburgh, got into the trendy glamping game this year by setting up on the grounds of Cove Pastures Flower Farm & Branch Bender Cidery in Accident, Maryland near Deep Creek.
Where to Stay: “Out of Africa” meets Ace Hotel in these ultra-luxurious safari tents outfitted with queen-sized beds, local artwork, lanterns (with charging ports, naturally, because how else would you feed the ‘gram?), rugs and seating — plus a potbelly stove for those nights when temperatures dip. And yes, there are hot showers and flushing toilets in what the website describes as “the tented safari bathroom of your dreams.”
Where to Eat: Yup, they take care of that, too. When Chef Kevin Hunninen isn’t preparing the farm-to-table feast, guest chefs from celebrated Pittsburgh restaurants make regular appearances. During summer, Hunninen’s menu included dishes like a summer vegetable pancake with local tomatoes and corn salad, with a main of trout or pork chop and grilled veg, pesto potatoes and lemon-herb oil. There’s also a bar pouring cocktails, wine, beer and cider.
What to Do: Weekend packages ($600 per person) through mid-October include accommodations for Friday evening through Sunday morning; a Friday welcome reception, plus all meals through Sunday brunch; and yoga and mindfulness sessions on Saturday and Sunday mornings. Add-on amenities include bar beverages, outdoor massages, and excursions like horseback riding, hanging out with goats or whitewater rafting. Some weekends on-site craft demos with local artisans and live music are offered as part of the package.
Virginia Beach for Artsy Vibes
The Gist: Sure, you can book a generic hotel room right on the main drag and party like it’s 1999, but there are more sophisticated sides to this beach city, including the many ways to take in its thriving arts culture.
Where to Stay: A work of art in its own right, The Cavalier Hotel (fall rates start at $159 per night) was built in 1927. The hotel reopened in 2018 after an $85 million restoration, pairing its glamour with modern amenities, including a luxurious pool area. For those on a less glitzy budget, try the Hilton Garden Inn Virginia Beach Oceanfront (fall rates run $121-$460 per night).
Where to Eat: Locals swear by Eat: An American Bistro, with dishes ranging from global to ultra-local, featuring menu items like My Mom’s Crab Cake. In the ViBe Creative District, a self-described arts hub, check out Esoteric, which — despite the name — has an approachable menu including a few options for kids.
What to Do: The annual Mural Festival tied up August 29, but fall travelers can still enjoy festival art via a walking tour. Dip into the Virginia Museum of Contemporary Art, which is running the “Summer of Women” exhibit through October 24. Visit from October 22-24, and you’ll also catch the 65th Annual Boardwalk Art Show. If you want to soak in some art but can’t give up the beach, visit during the International Sand Sculpting Championship, held this year from September 24 to October 3 in tandem with the city’s Neptune Festival, an arts and crafts show that runs from September 24-26. For an experience that marries sound with nature, head to Pleasure House Point Natural Area to soak in “SOUNDWALK,” a new self-guided, GPS-enabled public art hike with music composed by Pulitzer Prize-winning sound artist Ellen Reid.
Maryland’s Allegany County for Biking Fanatics
The Gist: The county seat of Cumberland, Maryland is where D.C.’s 184.5-mile C&O Canal towpath ends and the 150-mile Great Allegheny Passage (GAP) toward Pittsburgh begins, making it the perfect pitstop (or starting point) for cyclists.
Where to Stay: The Lodge at Rocky Gap resort, situated just inside Rocky Gap State Park near Cumberland, features recently updated rooms, a casino, golfing, a spa and mountain views. If you prefer something smaller, more chill and cyclist-friendly, try Town Hill B&B in Little Orleans.
Where to Eat: People, pay attention. There is an Allegany County Ice Cream Trail with nine stops strung between Little Orleans to Lonaconing. If you must eat something other than ice cream, hit up Princess Restaurant in Frostburg for classic diner food; The Queen City Creamery & Deli for casual breakfast and lunch options; or Puccini Restaurant in Cumberland for wood-fired pizzas and Italian-inspired favorites. The first two, incidentally, are also stops along the Ice Cream Trail.
What to Do: Those intrepid enough to bike the entire GAP will be richly rewarded with scenic valleys, mountains and rivers along the mostly level trail, all while crossing the Mason-Dixon Line, the Eastern Continental Divide, the Laurel Highlands and Ohiopyle State Park, ending at Pittsburgh’s Point State Park. Check in with local outfitters like Wheelz Up for gear, guidance and shuttle services. Don’t fret if you’re interested in visiting but cycling isn’t your thing. There’s also the Western Maryland Scenic Railroad, a heritage railroad that conducts a 16-mile return trip between Cumberland and Frostburg, with plenty to explore in each town.
Learn more about Maryland’s Allegany County on mdmountainside.
Strasburg, Virginia for a Chill Romantic Weekend
The Gist: The beauty of this tiny Virginia town in the Shenandoah Valley — aside from the picturesque mountain views and charming shopping strip — is that there really isn’t a ton to do (which is especially great if you need a little help in the slowing-down and unplugging departments).
Where to Stay: There are a few chain hotels within walking distance from downtown, but they’re not exactly what we would call romantic. Instead, consider booking one of the four new Spring Valley Cottages run by the adorable Woodbine Farm Market or maybe the Inn at Vaucluse Spring, a B&B with guest houses and private cabins on 44 gorgeous acres, located about 15 minutes up the road.
Where to Eat: Among the locally owned options, try Box Office Brewery, located in an old movie theater that serves indulgent bar foods like pulled-pork nachos and fried pickles, alongside brick-oven pizzas and sandwiches. Even the most diehard of coffee snobs will appreciate Nancy’s, a legit coffee and espresso bar on the main drag. And gourmet hot dogs and burgers can be found at The Doggery, where you can order a proper Chicago dog (yes, there are sport peppers and a poppy seed bun); a breakfast dog topped with hash browns, bacon, a sunny-side-up egg and cheese; or an Alamo dog loaded with refried beans, nacho cheese sauce, jalapeños, tomatoes and sour cream.
What to Do: Stay in your room and make out, of course. But after that, maybe tour some battlefields, do a little shopping and see if any quaint, quirky local festivals are happening, such as the annual Grilled Cheese + Tomato Soup Festival, held November 6 this year.
Bryce Resort for Family Fun
The Gist: Summer used to be considered off-season at ski resorts, but Bryce Resort in Bayse, Virginia, smartly celebrates all the seasons with activities like golfing, hiking and mountain biking, plus lake adventures like kayaking, canoeing and tubing.
Where to Stay: The resort doesn’t have its own accommodations, but nearby rentals are available through Chalet High and Creekside Realty. There’s also a pretty unique summer family camp called Shrine Mont in Orkney Springs, less than 10 minutes away from Bayse, that offers fall cabin rentals.
Where to Eat: The best way to start this trip is by stopping into the Route 11 Potato Chips factory in Mount Jackson to stock up on dill pickle-flavored chips. And for a tiny town in the middle of nowhere, there are at least two excellent restaurant options in Bayse Brew Hollow, a quaint little spot for sandwiches, pizzas and beers, and at RHouse Wine & Cafe, where husband and wife owners Gisela and Juan Lucca serve up wine, tapas and friendly vibes.
What to Do: Just like in winter, the offerings during the other three seasons here are decidedly outdoorsy. There’s an extensive downhill mountain bike park accessible through day passes, camps and lessons. And in the shadow of the mountain sits Lake Laura, where fall visitors can relax on the grassy beach. There’s also summer tubing, scenic lift rides, disc golf and a new family-friendly game called fling golf (and regular old golf).
Enjoy this piece? Consider becoming a member for access to our premium digital content. Support local journalism and start your membership today.