Cozy Autumn Weekend in Richmond, Virginia

Check into the 73-room Quirk Hotel, a boutique downtown Richmond property where art takes center stage with original works by local and national artists adorning the halls and guest rooms. The building itself is a converted 1916 department store, adding to the hotel’s charm and character.

From there, it’s an eight-minute drive to Carytown, the city’s eclectic shopping district. Pop in and out of indie shops, like Mongrel, a go-to for creative gift ideas and novelty finds; Shelf Life Books, for more than 45,000 preloved titles; and World of Mirth, a colorful toy shop for kids of all ages.

Next, take a 20-minute walk to the Virginia Museum of Fine Arts, home to more than 50,000 works of art that span nearly every significant world culture. Grab lunch to-go from a neighborhood favorite, like Greek on Cary or Coppola’s Deli, and enjoy a picnic in the museum’s scenic 3.5-acre sculpture garden.

Plan your trip around the fall festival calendar to see a concert. Catch the Iron Blossom Music Festival (September 20–21, 2025) at Midtown Green with headliners like Vampire Weekend and The Lumineers, or check out historic Jackson Ward during the 2nd Street Festival (October 4–5, 2025) for live music, local eats, and lively community vibes.

Kick off the day with a 10-minute drive to Scott’s Addition, a historic neighborhood celebrated for its street art, breweries, and thriving coffee scene, home to at least six indie coffee shops. Order a High Five, a signature espresso drink with a touch of sugar and topped with foamed half and half and sea salt at Grit Coffee, then explore colorful murals splashed across this lively neighborhood.

In fall, don’t miss the Scott’s Addition Pumpkin Festival (October 25, 2025), a family-friendly event with live music, craft beer, a costume contest, and a kids’ zone with rides, slides, and bounce houses. Another seasonal favorite is Hops in the Park at Henricus Historical Park (early November) for Virginia-made craft beer, local hops farmers, and a farmers’ market.

Later, drive seven minutes to the Canal Walk, a scenic stretch along the James River featuring historic canals, murals, sculptures, and memorials. Rent a bike at one of the RVA Bike Share stations or simply stroll. Cap off the evening at Maymont’s Garden Glow (October 15–November 9, 2025), when illuminated gardens and paths turn the estate into a magical fall wonderland.

Start your day with a 15-minute drive to Lewis Ginter Botanical Garden, where vibrant fall colors await, especially at the Flagler Garden and Grace Arents Garden. The Woodland Walk and Asian Valley also offer postcard-worthy views of reds and golds. Families will love the Children’s Garden for seasonal displays of pumpkins.

Afterward, it’s a short drive to SB’s Lakeside Love Shack, a playful spot with an all-day breakfast menu, live music, and a welcoming, homey vibe. Inspired by family recipes and the B-52’s Love Shack, menu items have inventive names like “Bang Bang on the Door” Benny and “Tin Roof Rusted” Hash.

Next, drive 15 minutes to Belle Isle, part of James River Park. An easy 1.8-mile loop features a suspension bridge, river rocks, a quarry pond, and Civil War–era ruins. Keep your eyes open for whitewater rafters navigating the James River.

Finish the day on Brown’s Island, home to trails, public art, and the annual Richmond Folk Festival (October 10–12, 2025), one of Virginia’s largest events, drawing visitors from across the country. Stages hosting folk, gospel, blues, and world genres fill the historic riverfront with melodic sounds.