In the second post of Great Places to Visit in Fall, we’re taking a trip around Long & Foster’s markets, exploring oceanside communities, booming cities and suburban towns and mountainside retreats that our agents say are amazing to not only visit in fall, but also to live year-round. While real estate agents often don’t get weekends off—those are prime home-shopping days—they shared with us what they’d do on an ideal weekend in their towns. 

Outer Banks, N.C.  

Fall brings out what Long & Foster agent Tammy Shilling calls the “true Outer Banks feel.” The weather is still warm enough for a beach day, but visitors encounter fewer crowds, shorter restaurant waits and far less traffic. “People think the Outer Banks is more for summer, but there’s really just so much to enjoy in the fall,” Shilling said.  

Head north to Corolla’s four-wheel-drive beaches for the chance to see the area’s wild horses, or look for marked sea turtle nests as the season winds down. Each Outer Banks town offers something different, whether it’s the waterfront boardwalk and jazz music in Duck, the beaches of Nags Head or the more remote landscapes farther south. 

Two October events offer especially good reasons to plan a weekend visit. The Outer Banks Parade of Homes, set for Oct. 8 to 10, gives visitors access to over a dozen newly built and remodeled properties from Corolla to Avon. It’s a favorite tradition for Shilling, who makes a weekend of touring the homes and exploring the different communities along the way. Food lovers can visit the following weekend for the Outer Banks Seafood Festival, held Oct. 17 in Nags Head. The festival celebrates the region’s seafood, fishing heritage and coastal culture. 

No fall trip to the Outer Banks is complete without spending time in Manteo, a destination Shilling believes too many beachgoers overlook. Located on Roanoke Island, the walkable waterfront town offers locally owned shops, galleries, restaurants and small-town charm just a short drive from the ocean. Plus, make sure to plan a meal at JK’s in Kill Devil Hills or Steamers in Southern Shores.  

As Shilling said of fall on the Outer Banks, “You have the Outer Banks back to yourself. You don’t have the lines or the traffic, but you still have warm weather and lovely beach days.” 

Thurmont, Md.  

Tucked into the foothills of the Catoctin Mountains, Thurmont offers a fall weekend filled with brilliant foliage, outdoor adventure and small-town charm. Long & Foster agent Tyler Charles suggests staying about 10 miles north in historic Emmitsburg, where visitors can have dinner at longtime favorites such as the Carriage House Inn or Ott House before taking the scenic roads toward Thurmont.  

“It’s the gateway to the mountains,” Charles said. “Driving around Thurmont and Emmitsburg in the fall is just absolutely beautiful.” 

The next day, head to Catoctin Mountain Park or plan a hike to Cunningham Falls and a picnic beside Hunting Creek Lake, a favorite childhood tradition for Charles and his family. The surrounding mountains and Frederick Watershed offer miles of hiking trails, scenic overlooks and some of Maryland’s best fly-fishing, particularly in fall. Families can also visit the Catoctin Wildlife Preserve, while those visiting during the annual Catoctin Colorfest will find Thurmont filled with vendors selling everything from local maple syrup to handmade crafts. Mountain Gate Family Restaurant, a longtime local favorite known for its country-style buffet, is an easy stop after a day outdoors. 

Visitors with extra time can explore more of Frederick County, from the overlooks at Gambrill State Park to Sugarloaf Mountain, where hiking and rock climbing can be paired with a meal at the nearby Comus Inn or a visit to Sugarloaf Mountain Vineyard. Springfield Manor Winery, Distillery and Brewery, set against the mountains near Thurmont, offers another picturesque place to unwind. With Gettysburg and downtown Frederick all within easy reach, the area blends nature, history and local flavor.  

“It’s a hidden gem,” Charles said. “Whether you’re an outdoorsman who enjoys hiking and fishing, a history buff or someone who just wants to explore the lakes and springs throughout the mountains, there’s so much here to experience in the fall.” 

Winston-Salem, N.C. 

“Winston-Salem is really known for arts and innovation,” said Kaitlin Eller, a managing broker with Long & Foster Real Estate, and a fall weekend here offers a chance to explore the history that helped shape that creative spirit.  

Start Saturday in Old Salem, touring the restored buildings, strolling through the central square and stopping at Winkler Bakery for a slice of its signature Moravian sugar cake. Take a coffee break at Lot 63 and visit the covered bridge, a favorite local backdrop for family photos. For a seasonal twist, book a family-friendly ghost walking tour to hear some of the city’s spookier stories. Later, head to Innovation Quarter, where the city’s industrial history meets its creative present. Explore Bailey Park and check out the local events calendar for outdoor movies or community activities before settling in at Graylyn Estate, a historic boutique hotel with 55 acres of grounds. 

Spend Sunday at Reynolda Village. “My absolute favorite place to visit is Reynolda Village. Growing up, we would go there often, and even now, it’s still a destination for us,” Eller said. Begin with coffee and hot, made-to-order cake doughnuts at Dough-Joe’s Doughnuts & Coffee, then browse the boutiques and walk the grounds of the historic Reynolds family estate. Stop at Theodore’s Bar & Market for fresh sandwiches and salads before visiting Reynolda House Museum of American Art, which opens in the afternoon on Sundays. Leave time to explore the gardens and walking trails for a relaxing finish to your fall getaway to Winston-Salem. 

St. Michaels, Md. 

“There’s so much to do in our little town that people are always busy,” said Cornelia Heckenbach of Long & Foster. 

Start Saturday with coffee and breakfast at Sprout, then browse the St. Michaels Farmers Market for local produce and baked goods before exploring the town’s many unique independent shops. Spend the afternoon at the Chesapeake Bay Maritime Museum, where the waterfront campus and interactive exhibits bring the region’s history to life. For dinner, reserve a table or grab a seat at the bar at Ruse, a favorite of Heckenbach’s for its creative use of local produce and its inviting, fun atmosphere. 

On Sunday, take a leisurely walk along the St. Michaels Nature Trail, following the former railroad route, then head to the harbor to watch the boats and enjoy lunch at Foxy’s Harbor Grille. You can also stop by the Classic Motor Museum of St.  Michaels to see its collection of mint-condition cars and support the museum’s mission to help train the next generation of auto service technicians. Later, spend some time outdoors along the town’s main street, stopping by Limoncello for Italian food and outdoor seating where you can watch visitors stroll by. A Miles River cruise, like those from Patriot Cruises, offers another perspective on the area’s spectacular waterfront homes and scenery. 

For an extra dose of fall fun, plan your visit around Fall Into St. Michaels, Oct. 17–18, with pumpkin carving, seasonal activities and the annual Jack Russell races, or OysterFest on Nov. 7. The latter features oysters prepared in a variety of ways, live music, boat rides and family activities, a festive way to experience the area’s food and traditions.