Fall is the best time of year for hiking, relaxing on the beach, and attending one of the many fall festivals in our part of the state. Here is our comprehensive list of fun things to do in Southern Delaware this fall.
Book your fall stay at our Mansion Farm Inn in Milton, where you’ll enjoy the country views mere minutes from downtown historic Milton and the nearby coastal towns of Lewes and Rehoboth Beach.
Fall Festivals in Southern Delaware
Discover the vibrant fall scene in Southern Delaware with a mix of cultural, culinary, and festive events! With craft beer festivals, autumn train rides, and spooky Halloween celebrations, our neck of the woods is full of fall excitement. Here are some of the events you won’t want to miss:
September
If you plan to visit in September, make sure you come hungry! Oktoberfest and fall harvests mean lots of apples, beers, and Bratwurst!
- Delaware Saengerbund Oktoberfest
- Join the annual Oktoberfest in Newark the first weekend after Labor Day. Enjoy German specialties like Bratwurst, Weisswurst, BBQ chicken, pretzels, live Bavarian music, and dancing. Shop unique imported gifts and souvenirs while savoring traditional treats such as potato pancakes and plum cake.
- Amish Country Bike Tour
- Delaware’s first urban “park without boundaries” is in Dover’s historic district. Hop on a bike and explore two dozen historic and culturally significant sites, like the 300-year-old Dover Green and the John Bell House dating to the 1700s.
- Fall Fun at Fifer’s
- Challenge yourself to their 6-acre corn maze. Pick your apples in September and your pumpkins in October.
- Brandywine Festival of the Arts
- This annual arts festival in Wilmington, Delaware, is the largest in the state and takes place the weekend after Labor Day. Participants from all over the U.S. offer their artistic wares, and there are plenty of food and snack vendors.
- Hagley Car Show
- Explore decades of automotive innovation as you admire 500+ antique and restored cars that date back to the early twentieth century. The festival includes a vehicle parade, lively motoring music, and a food court.
October
Get into the Halloween spirit this October with Delaware’s finest spooktacular events! Zombie Fest and the Sea Witch Festival are just a few of the events in the area. Here are some of our favorite October events near Lewes and Rehoboth Beach:
- Zombie Fest
- The town of Milton’s annual Zombie Fest has costume contests, live music, vendors, zombie makeup stations, and, of course, the Zombie Walk parade!
- Delaware Beer Fest
- Join the Delaware Beer Fest to sample local and national brews, enjoy live music, and savor food from local vendors. Test your skills with Giant Jenga, enjoy Beer Fest Trivia, and capture memories at the photo booth.
- Wilmington and Western Railroad Autumn Leaf Special
- All aboard! Choose from two different leaf-peeping train excursions for beautiful fall scenery.
- Annual Rehoboth Fall Sidewalk Sale
- One of the best Rehoboth Beach events for those who like shopping! Sidewalk shop for discount deals and fabulous finds, rain or shine, at Rehoboth Beach & Dewey Beach Resort Area.
- Lewes’ Craft Fair
- Lewes’ annual craft fair returns for a weekend of arts, crafts, food, and music.
- Rehoboth Beach Jazz Festival
- Join the fun for four days of great live music. Come for the food, tax-free shopping, the beautiful beach, and, of course, the music.
- Hagley Craft Fair
- This marketplace features talented artisans displaying and selling fine arts, crafts, and gourmet items. Refreshments are available from local food trucks, including the Wilmington Brew Works Beer Garden.
- Sea Witch Festival
- Join in the sea witch fun as thousands gather to enjoy this annual festival, which includes a costume parade, a bandstand full of live music, area artisans and vendors, and magic shows.
November
As fall gives way to winter, Southern Delaware offers diverse events to celebrate the season’s transition. Here are some fun things to do in Southern Delaware this fall for November:
- First State Heritage Park Colonial Market Fair
- This fair brings the past to life with living history, trades and crafts demonstrations, and entertainers. Walk the ground where 18th-century Doverites went to market as you browse, shop, listen, and learn.
- Rehoboth Beach Independent Film Festival (RBIFF)
- RBIFF is Delaware’s oldest and largest film festival. Take it all in with various American and international features, documentaries, and short films.
- Rehoboth Art League Annual Holiday Fair Fine Craft Show
- The Annual Holiday Fair Fine Craft Show will feature a variety of artisans displaying and selling their work, including unique jewelry, glasswork, ceramics, decorative and wearable fiber creations, and more. Stroll, browse, shop, and enjoy refreshments from local favorites Point Coffee House Bake Shoppe and Dogfish Head.
Hit the Beach in Southern Delaware the Fall
Autumn in Southern Delaware is one of the best times to hit the beach. The mile-long Rehoboth Beach Boardwalk is one of the area’s most famous beach attractions. After your walk, you can catch a live show at Clear Space Theater or shop at the Rehoboth Beach Farmers Market. Avoid crowds and head to Savannah Beach or Johnnie Walker Beach in Lewes. Younger beachgoers will enjoy the go-karts and water slides at Midway Speedway Park.
If relaxing on the beach isn’t your thing, check out Southern Delaware’s trails. Visitors can walk, bike, sail, run, or birdwatch on Delaware’s coastal trails, such as Gordons Pond and Junction and Breakwater Trail. Check out these state parks to get in on the local autumn action:
- Cape May-Lewes Ferry
- Cross the Delaware Bay in style on the Cape May-Lewes Ferry. You’ll see historic lighthouses, picturesque harbors, oceangoing vessels, unique seabirds, and possibly dolphins! You’ll also appreciate their welcoming terminals with restaurants, lounges, and gift shops!
- Lightship Overfalls
- This historic national landmark on the canal offers memorable ship tours and unique items to browse at the Ship Store.
- Cape Henlopen State Park
- Situated at the mouth of Delaware Bay, this beautiful park has over 6 miles of coastline. Try swimming, boating, fishing, kayaking, clamming, paddleboarding, windsurfing, hiking, or biking.
- Fort Miles Historic Area at Cape Henlopen State Park
- Fort Miles Museum and Historic Area is a special place for history buffs, veterans, or anyone interested in learning about Delaware history. The fort sits on a high bank overlooking the Atlantic Ocean and is surrounded by rolling sand dunes.
- Mary Vessels Park
- This quaint park is an ideal place to stop and rest under the shade of a large magnolia tree and eat an ice cream cone as you watch the people stroll by.
- Stango Park
- Serving as the gateway to Lewes, this park is also home to the Lewes Public Library. During the fall, pack a picnic or sit and read a book as you enjoy nature’s calming sights and sounds.
- George H. P. Smith Park
- Located at the end of Dupont Avenue, this charming park features a shady pond with native flora and fauna, a butterfly garden, a walking path with benches, a horseshoe pit, fishing spots, and grills and picnic tables.
- Blockhouse Pond
- Fish for largemouth bass, summer flounder, and striped bass in this well-maintained lake. There is a nice trail around the water and plenty of benches as you sit and admire the views.
- Edward H. McCabe Preserve and Greenway Trail
- This 140-acre nature and wildlife sanctuary offers three miles of hiking trails. Along the way, you can spot over 100 species of birds. In addition to May and June, September and early October are peak months for birdwatching. Access the preserve by the nearby parking lot or canoe, which you can rent at Wilson’s Sunshine Marina.
Immerse Yourself in Southern Delaware History
Looking for a famous landmark in Delaware? History buffs can immerse themselves in local history at these Southern Delaware historic sites and landmarks:
- Fisher Martin House
- The gambrel-roofed Fisher Martin House dates back to 1730 and was sold to Rev. James Martin, a minister of Cool Spring, Indian River, and Lewes Presbyterian churches. The home stayed in the Martin family for over two hundred years.
- Zwaanendael Park & Herb Garden
- Home to the Zwaanendael Museum, the 18th Century Fisher Martin House, and the Lewes Chamber of Commerce and Visitor’s Center, this park features a central fountain surrounded by benches where you can sit and relax amidst nature. Check out the Fisher Martin Herb Garden, an authentic 1700s Colonial herb garden with herbs that Colonial housewives used for culinary, medicinal, and other household uses.
- Cannonball House
- Named for the damage it sustained during the U.S. Civil War, the Cannonball House is on the National Register of Historic Places. Built in 1853 as a planter’s townhouse, you can tour the house and gardens and shop for original items at the Gift Shop.
- Lewes History Museum
- The Lewes History Museum presents thousands of historic artifacts, artwork, documents, maps, and photos for your enjoyment.
- Lavender Fields Farm at Warrington Manor
- Wander through rows of lavender flowers on this historic 5-acre farm. The manor is just a few miles from Lewes and Rehoboth Beach and is open until December 31.
- Rehoboth Railroad Station
- Built in 1879 after train service was extended to Rehoboth Beach, this historic building has since been moved and revitalized. As you browse the station, you’ll find helpful travel information for your Southern Delaware vacation.
- Rehoboth Beach Museum
- This unique museum offers historical walking tours and an Annual Beach Ball.
Now that you have plenty to see and do in Southern Delaware in the fall, BOOK A COZY GUEST ROOM at our Mansion Farm Inn. You’ll enjoy a peaceful setting, a heated in-ground pool (April 15 to Oct 31, depending on the weather), and a delicious breakfast each morning.
