In this new blog series, 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.  

Richmond, Virginia.  

Richmond is best explored neighborhood by neighborhood. As Margaret Wade, Long & Foster’s No. 1 agent, puts it, “Richmond is a city of neighborhoods. There are just so many charming neighborhoods with architectural integrity and community. It’s a great place to live and also visit for the weekend.”  

Start Saturday at the farmers market at St. Stephen’s, then explore Carytown, where you’ll find a lively collection of independent restaurants, boutiques and specialty shops. Browse local favorites such as Roan and Crème de la Crème and take in the nostalgic atmosphere of the historic Byrd Theatre. 

Spend the afternoon at The Valentine, a museum devoted entirely to Richmond’s history, people and neighborhoods. Visitors can tour the historic Wickham House or join one of the museum’s walking tours, which explore the city’s past beyond its best-known landmarks. From there, head toward the James River for a walk across the T. Pott Bridge or along the riverfront. Stay into the evening to see the interactive digital art installation lighting the new CoStar building, a striking addition to the riverwalk after dark. Plus, make sure to try one of Wade’s favorite restaurants: Stella’s for Greek-inspired dishes, Grisette in Church Hill and Shagbark near Libbie Mill. 

On Sunday, enjoy Richmond’s fall color at Maymont, where the grounds include landscaped gardens, open lawns, historic buildings and an animal farm or venture onto the James River Park System’s trails at Belle Isle or Pony Pasture. Leave plenty of room for Richmond’s locally driven restaurant scene. For your Sunday outing Wade recommends Uliveto or Bacchus in the Fan and Janet’s Café and Bakery in Westover Hills.  

“You never need to go to a chain restaurant here in Richmond,” Wade said. It’s a fitting summary of a city where independent businesses, creative chefs and distinct neighborhoods give visitors more than enough to fill a weekend. 

Chincoteague, Virginia.  

Fall on Chincoteague Island is what Meghan O. Clarkson calls “the locals’ summer, ”a season of beautiful weather, lighter crowds and abundant wildlife. “September and October are just a big hug,” she said. “Your stresses go away.”  

Start Saturday morning on the water with a kayak excursion or boat tour for a closer look at the island’s scenery and wild ponies. With Chincoteague situated along major bird and monarch migration routes, fall brings exceptional opportunities for bird-watching and wildlife photography. Spend the afternoon at the beach or exploring the trails at Chincoteague National Wildlife Refuge before enjoying dinner at AJ’s on the Creek or Blackfin Island Grill, followed by ice cream from Island Creamery or a soft-serve at Mister Whippy. 

Visitors can make the weekend even more memorable by timing their trip around one of Chincoteague’s popular fall events. The Chincoteague Oyster Festival, held Oct. 10 in 2026, celebrates the start of oyster season with fresh local seafood and live music. Before choosing a weekend, visitors should also check the launch schedule at NASA’s Wallops Flight Facility to see if they could fit in a rocket launch viewing. 

Save time for the Museum of Chincoteague Island, which shares the people, industries and traditions that shaped the community. “One thing I wish people knew more about is our heritage and what it was like before we were a tourism town,” Clarkson said, pointing to the island’s former fishing and poultry industries. After touring the museum, browse the shops downtown and in the revitalized Village Mall, then end the day with sunset at Donald J. Leonard Park or a walk to the Island Waterman’s Memorial.  

“Chincoteague is just a healing place,” Clarkson said. “As soon as people pass the NASA visitors center, they can feel the anxiety drain from their bodies.” 

New Hope, Pa. 

New Hope offers the kind of fall weekend best enjoyed on foot. “It’s a great walking town, with shops and pubs and restaurants,” said Long & Foster agent Kris Shields.

Begin on Main Street, which runs alongside the Delaware River, browsing the town’s eclectic shops before stopping for lunch or a drink. From there, walk across the New Hope-Lambertville Bridge into Lambertville, N.J. While New Hope can be busy during the fall, Lambertville offers a somewhat quieter atmosphere, along with independent restaurants, antique shops and streets lined with colorful Victorian homes. As Shields advises, “If you go to New Hope, you need to go to Lambertville, too.” 

Fall is an especially fun time to explore both river towns. In Lambertville, the elaborate Halloween displays along North Union Street have become a popular attraction. Back in New Hope, visitors can bike or walk for miles along the Delaware Canal towpath or take in the Bucks County countryside aboard the New Hope Railroad’s 90-minute Fall Foliage Excursion. The railroad also offers seasonal themed rides, while the historic Bucks County Playhouse presents professional productions in a former gristmill overlooking the river. 

Much of New Hope’s appeal comes down to its atmosphere. “People go for the vibes, the restaurants and the shopping,” Shields said. Stay or dine at the historic Logan Inn in the center of town, enjoy river views and live entertainment at River House at Odette’s, or step inside The Salt House, an intimate restaurant known for its stone walls, low ceilings and old-world character. Together, New Hope and Lambertville offer the ideal mix of fall scenery, historic architecture, local dining and small-town energy, all within an easy drive of Philadelphia.