Why You Should Consider Wilmington for Fall Pleasures

Wilmington, Delaware. We know, we know—Dela-where? Despite being situated in the second smallest state in the country, the greater Wilmington area and Brandywine Valley offer an abundance of history, culture, and fun seasonal experiences that travelers might not expect.

Visitors can leaf-peep, hike and bike in Brandywine Creek State Park, White Clay Creek State Park and Ashland Nature Center; sip fall cocktails on The Riverfront; go for a hay ride at a family farm established in 1860, or enjoy the crisp autumn air while strolling the brick streets of Historic New Castle by the water at Battery Park.

For after-dark thrills, venture on a Hauntings in History Tour that takes guests inside one of the most haunted mansions in Old New Castle. Ramsey’s Farm is a quintessential fall destination with pumpkin patches, hayrides, and a corn maze, plus extras like goat yoga, floral classes, and bonfire nights.

Since it is located in the first state, Wilmington offers travelers a chance to glimpse into history when they visit destination staples like the duPont Estates, especially Winterthur, a museum, garden, and library located in Wilmington on a 1,000-acre estate that was once the du Pont family home. It houses a vast collection of American decorative arts, features extensive naturalistic gardens, and offers various programs and events, making it a significant cultural and historical site in the region.

For lovers of cultivated nature, there are the famed Longwood Gardens (be sure to check out the seasonal chrysanthemums). And, of course, the covered bridges throughout the region—there are three in particular worth seeking out: Ashland Covered Bridge, the oldest original covered bridge in Delaware, built in 1860–a one-lane lattice truss; Wooddale Covered Bridge, originally built in 1850, destroyed in 2003 and rebuilt; and Smith’s Bridge, the longest covered bridge in Wilmington, a 154-foot Burr arch-truss spanning Brandywine Creek near the PA line.

What’s Queer About Delaware?

Plenty, as Wilmington, DE has a diverse and vibrant queer community, supported by LGBTQ+-friendly businesses. These include the Crimson Moon bar and drag venues like The Queen, community groups like Our Night Out Wilmington (ONO), and cultural institutions like the City Theater Company. We hear The Mercury Cafe and Teahouse is run by partners Dwayne and Aaron, and that Wings & Thai Station is very LGBTQ-friendly.

The area also boasts a rich queer history, with foundational activists like Barbara Gittings, Ivo Dominguez Jr., and James C. Welsh shaping the region’s progressive policies and culture. There’s also DeShanna and Trinity Neal, a mother and daughter from Wilmington, who are known as transgender rights advocates in Delaware.

Quick Round-up of Fall Events

9/6 – Historic Odessa Brewfest: Sample regional and national craft beers, local wine and spirits, plus food, music, and community fun.

9/21 – Hagley Car Show: 500+ cars from the 1900s–1990s, plus a parade, food trucks, and the Du Ponts Down the Road exhibition featuring historic vehicles like a 1918 Cadillac.

9/21-23 – Oktoberfest–Delaware Saengerbund: Enjoy bratwurst, pretzels, potato pancakes, and Bavarian music and dance. $10 admission includes unlimited rides.

10/9-12 – Wilmington International Film Festival: The 17th Annual Film Brothers Festival of Shorts with screenings, curated art, and live music.

10/11 – The River Towns Ride & Festival: A cycling event through Delaware’s historic river towns with medals, live music, food, and beer at the post-ride festival in Battery Park.

10/18 – Hagley Craft Fair: Shop fine arts, crafts, and gourmet foods from top Mid-Atlantic artisans.

11/6-9 – Diamond State Black Film Festival: Showcasing films by and featuring People of Color, with workshops, panels, and master classes for emerging filmmakers.11/7-9 – Delaware Antiques Show: One of the nation’s top antiques shows, with 60+ distinguished dealers highlighting American antiques and decorative arts.

For a complete breakdown of leaf-peeping destinations, historic sites, and fall events and festivals, you can view the official Greater Wilmington, Delaware Fall Guide.

Here are the 10 best LGBTQ-friendly hotels to stay at in Wilmington, DE.