Fun Things to Do in Southern Delaware this Fall

There are more than beaches in Delaware! Here is a comprehensive list of fun things to do in Southern Delaware this fall. From high’s in the upper 70’s in September to low’s in the 40’s in November, the weather provides opportunities for fun both indoors and out. Book your stay at our Mansion Farm Inn in Milton, where you’ll enjoy the country views, yet you’ll also be just minutes from downtown historic Milton and the nearby towns of Lewes and Rehoboth Beach.

Fall Foliage in Southern Delaware

The primary reason to visit Southern Delaware during the fall is glorious fall foliage. Enjoy the vibrant beauty of leaves reflected on the water at such secluded natural settings as Trap Pond State Park, Killens Pond State Park (featuring a nature center and regular hayrides), or Lums Pond State Park. For bird lovers, Bombay Hook National Wildlife Refuge is perfect for spotting native and migrating birds of all kinds. Take a scenic drive on miles of country roads where you take it all in while listening to your favorite tunes and sipping a hot cup of coffee or cocoa. It’s a magical way to spend the day!

Fall Festivals in Southern Delaware

September

• Amish Country Bike Tour – Delaware’s first urban “park without boundaries” is located 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.
• First Friday Fun Nights at Schellville – Schellville has been known for its winter festivals for a long time, but now offers First Friday Events. Join the fun from 5-9pm for food trucks, hospitality tent and beer garden, live music, roller skating, and artisan shacks full of merchandise. Sip, sample, shop, and skate to your heart’s content.
• Brandywine Festival of the Arts – 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, along with plenty of food and snack vendors.
• Delaware Saengerbund Oktoberfest – The first weekend after Labor Day in Newark, is the annual Oktoberfest. The festival opens Friday at 5pm with the opening parade at 7pm. Join the fun Saturday from Noon to 11pm and Sunday from Noon to 6pm. Savor the flavors of German specialties, like grilled Bratwurst (pork sausage), Weisswurst (veal sausage), BBQ chicken, potato pancakes, pretzels and “Rollmops” (a marinated herring served with rye bread), potato salad, and sauerkraut, a variety of torten, and traditional plum cake. Live entertainment includes Bavarian dancing and German music. Shop from unique imported gifts and souvenirs.
• End of Season Beach Party in Dewey Beach – Join the annual end-of-season party on the beach with plenty of food and drinks.
• 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.
• Fall Fun at Fifer’s – Challenge yourself to their 6-acre corn maze, pick your own apples in September, and your pumpkins in October.
• Bikes and Beers Delaware 2022 – This September, bike 15, 30, or 45 miles through the beautiful area of Lewes, then enjoy a festival full of craft beers, live music, a charity raffle and more! All riding levels are welcome!

October

• Delaware Beer Fest – Saturday, October 1, 2022 from Noon to 6:30pm is this year’s Delaware Beer Fest where you can sample beer from both local breweries and national brands. Listen to live music as you browse the wares of local artisans. Enjoy delicious food from local restaurants and food trucks. Try your hand at Giant Jenga or a round of corn hold. There will be Beer Fest Trivia as well as Photobooth Fun to capture the memories.
• Wilmington and Western Railroad Autumn Leaf Special – Choose from two different leaf-peeping train excursions: 1) MT. CUBA PICNIC GROVE is a 1½-hour round-trip ride. Pack a picnic lunch or buy food and drinks at Greenbank Station to enjoy during the stop. 2) HOCKESSIN is a 2½-hour round-trip journey that travels the entire 17-mile length of the railroad to the town of Hockessin where you can shop the local shops and buy food from one of several eateries near the tracks for the trip back.
• Annual Rehoboth Fall Sidewalk Sale – Sidewalk shop for discount deals and fabulous finds, rain or shine, at Rehoboth Beach & Dewey Beach Resort Area
• Lewes Craft Fair – Lewes’s annual craft fair returns October 1, 2022 for a day of arts, crafts, food and music.
• Rehoboth Beach Jazz Festival – Join the fun October 13-16, 2022 for 4 days of great live music. Come for the food, tax free shopping, the beautiful beach, and of course the music.
• Hagley Craft Fair – On October 16, 2022, this marketplace features talented artisans displaying and selling fine arts, crafts, and gourmet items. Refreshments are available from a variety of local food trucks, and the Wilmington Brew Works Beer Garden.
• Sea Witch Halloween & Fiddler’s Festival – October 28 – 30, 2022 will be full of sea witch fun as thousands gather to enjoy this annual festival, which includes a costume parade, bandstand full of live music, area artisans and vendors, magic shows, and so much more.
• Fall Fun at Fifer’s – Challenge yourself to their 6-acre corn maze, pick your won apples in September, and your pumpkins in October.
• Great Delaware Pumpkin Carve Festival – Look in awe at giant carved pumpkins, some weighing over 150lbs!. There will be food and drinks, haunted barns, a costume contest, trick-or-treating, hayrides, a bonfire, Delaware-made crafts for sale, and much more!

November

• First State Heritage Park 18th Century 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 is the oldest and largest film festival in Delaware. Take it all in from November 7 – 13, 2022 with a wide variety of American and international feature, documentary and short films.
• Rehoboth Art League Annual Holiday Fair- Fine Craft Show – The Annual Holiday Fair Fine Craft Show will be held November 5 and 6, 2022, and 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 the Point Coffee House and Bake Shoppe and Dogfish Head.
• Winter WonderFest – From November 19 through December 31, 2022, you can shop for coastal Christmas trees, drive through one mile of twinkling and colorful light displays, visit Mr. & Mrs. Claus, and skate on the WonderRink.

Things to do in Southern Delaware the Fall

Milton, DE

Our small, historic town is teeming with things to do during the fall months. Everything is also conveniently located just a few minutes away from our coastal B&B in the country.

• Edward H. McCabe Preserve and Greenway Trail – This 140-acre nature and wildlife sanctuary offers three miles of hiking trails. Along the way, you have an opportunity to 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 by canoe, which you can rent at Wilson’s Sunshine Marina
• Lavender Fields Farm at Warrington Manor – Wander through rows of beautiful, scented lavender on this 5-acre,  historic farm They’re just a few miles from Lewes and Rehoboth Beach and are open every day from 10am to 4pm from April 1 – December 31.
• Prime Hook National Wildlife Refuge – Unplug from the stresses of modern society and reconnect with your natural surroundings as you take a scenic drive on the four county roads, or walk the 7.5 miles of hiking trails. Birding and photography are fabulous here.
• Sports at the Beach – This 95-acre baseball facility features 16 individual, fully lighted fields where spectators can enjoy good ol’ American baseball as well as an on-site concession stand.
• Georgetown Speedway – Experience the thrill of the race with one of several pecialty races during September and October.
• Magnolia Street Antiques – This charming antique store offers a variety of home decor, from old to new and from simple to elegant.
• Milton Historical Society – Browse exhibits and collections that date all the way back to the 1600s at this small, but mighty historical society and museum.
• The Milton Theatre – Located in historic downtown Milton, this theater features a wonderful line-up of live performances as well as snacks, food, drinks, and a bar. Sit through the entire show in comfort in their new modern seats with memory foam
• The Rookery Golf Club South – Grab your clubs and challenge yourself to 18 holes of championship golf at this 4-star rated course.

Lewes, DE

• Lewes Beaches – Spend a fun day in the sun with swimming, fishing, boating, and other water sports at one of two beaches in Lewes: Savannah Beach or Johnnie Walker Beach.
• 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 that offers memorable ship tours, and unique items for browsing at the Ship Store.
• Cape Henlopen State Park – Situated at the mouth of the Delaware Bay this beautiful park has over 6 miles of coastline. Experience swimming, boating, fishing, kayaking, clamming, paddle-boarding, 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. You’ll find the site as beautiful as it is interesting.
• Mary Vessels Park – This quant 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 the calming sights and sounds of nature.
• 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, as well as grills and picnic tables.
• Blockhouse Pond – Fish for largemouth bass, summer flounder, and striped bass in this well-maintained lake. There is a nice trial around the water and plenty of benches as you sit and admire the views.
• Fisher Martin House – Dating to 1730, this gambrel-roofed house 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 and the 18th Century Fisher Martin House, which is also 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 1700’s Colonial herb garden with herbs that were used by Colonial housewives 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 listed on the National Register of Historic Places. Built in 1853 as a planter’s townhouse, you can take a tour of the house and gardens and shop for original items at the Gift Shop.
• Lewes History Museum – The Lewes History Museum presents tens of thousands of historic artifacts, artwork, documents, maps, and photos for your enjoyment.
• Hopkins Farm Creamery – Savor every drop of fresh farm made ice cream at this creamery that features award-winning sweet treats.
• Nassau Valley Vineyards – Delaware’s first and only award winning winery, you’ll find yourself a world away as you admire the verdant fields and sample their delicious wines.
• Historic Lewes Farmers Market – This community gathering place is ideal to shop for the freshest foods available from local farmers.
• Heritage Antiques – Browse 10,000 square feet of antiques and collectibles, including fine porcelain, glass, pottery, lighting, old tools, furniture, wall art, and much more.
• Lewes Mercantile Antiques –  Located on Second St. in Downtown Lewes, browse and shop the wares from over 30 dealers. The diverse inventory includes antique, vintage, collectible, retro, modern, and reproduction items.

Rehoboth Beach, DE

• Rehoboth Beach Boardwalk – This charming mile-long boardwalk is one of Rejoboth’s most popular attractions, and not just for summer. During the fall, you can still enjoy the many eclectic shops, restaurants and businesses along the boardwalk.
• Gordons Pond – This popular biking, hiking, running, and birdwatching trail is surrounded by area salt marshes as well as plenty of nature and wildlife.
• Junction and Breakwater Trail – Take a walk or bike ride on this coastal trail that boasts fabulous views and a peaceful setting.
• Lake Gerar –  This 15-acre park offers a freshwater lake, play area, fishing pier, trails, landscaped garden, and open space – perfect for a fall day spent in the great outdoors.
• Grove Park – Grove Park is surrounded by large trees and features a wide walking path, two pavilions, restrooms, shuffleboard courses and several park benches. It’s a wonderful place to relax with family and friends.
• Stockley Street Park – Charming little park where you can cross over the tail end of Silver Lake via Turtle Bridge, a pedestrian bridge from where you can admire the ducks and fish.
• Dune Nature Park – This small park is a preserve for native dune grasses and offers a place to stroll and admire nature as it connects Rehoboth Beach with the Boardwalk.
• Indian River Life-Saving Station Museum at Delaware Seashore State Park – The Life-Saving Station was built in 1876 for use by the United States Lifesaving Service and has recently been meticulously restored to its 1905 appearance. Tour the station, browse the museum, and shop for souvenirs at the gift shop.
• Indian River Marina – Rent a boat for the day and then grab a burger at Geronimo’s Bar & Grill.
• Revelation Craft Brewing Company – Sample and savor the highest quality brews made with passion and great craftsmanship.
• Clear Space Theatre – Catch a show at this live theater at the beach!
• Midway Speedway Park – Talk about a place of fun. Go-karting, super-fast water slides, an activity pool, lazy river, and large Olympic size recreational pool, mini-golf… need we say more?
• Rehoboth Beach Farmer’s Market – Shop for a wide variety of local produce and items at this outdoor farmer’s market.
• Tanger Outlets Rehoboth Beach – Shop ‘til you drop for a variety of discounted clothing, accessories, and more.
• Penny Lane Mall – Shop some more at this European inspired, open-air mall that offers a variety of shops.
• 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 also find helpful travel information for your Southern Delaware vacation.
• Verrazzano Monument – While strolling along the Rehoboth Boardwalk, take a quick history stop by honoring Italian Explorer Giovanni de Verrazzano, the first European explorer to chart portions of the East Coast.
• Rehoboth Beach Museum – This unique museum offers historical walking tours and an Annual Beach Ball (as in dancing).

Now that you have plenty to see and do in Southern Delaware in the fall, book your cozy guest room at our Mansion Farm Inn. You’ll enjoy a peaceful setting, heated in-ground pool (April 15th to Oct 31st depending on Weather), and delicious breakfast each morning.