12 Things To Do in Middletown, Delaware

Last Updated on March 3, 2024 by Emily Johnson

Nestled along the banks of the beautiful Appoquinimink River in northern Delaware, Middletown offers visitors a charming small-town atmosphere with plenty of things to see and do. From exploring historic downtown filled with quaint shops and restaurants to immersing yourself in nature at multiple state parks, Middletown has something for everyone.

As Delaware’s fastest growing area, the town has worked hard to preserve its history while continuing to add new attractions and events for both residents and visitors. Whether you’re looking for outdoor adventures, family fun, or want to learn more about Middletown’s roots that date back to the early 1650s when it was originally called “The Town in the Middle”, this guide will highlight 12 of the best things to do in Middletown, Delaware.

Explore Downtown Middletown

The heart of Middletown lies in its endearing and historic downtown centered around Broad Street and Main Street. Take a leisurely stroll as you browse through more than 30 specialty shops featuring antiques, books, home goods, and artisan-crafted gifts. Pop into one of the many excellent restaurants and cafés interspersed throughout downtown for a quick bite or longer dining experience showcasing international flavors and fresh local ingredients.

Don’t miss the Old Town Hall located right on Main Street. Now operated by the Middletown Historical Society, this Italianate-style building constructed in 1860 offers exhibits highlighting Middletown’s unique place in Delaware history. Just across the street sits the Middletown Train Station, built in 1886 and fully restored to its original Victorian beauty. Trains no longer run on these tracks, but you can still admire the exterior historic architecture.

As you explore downtown Middletown, keep your eyes peeled for 14 different murals created by local artists depicting iconic scenes and legends. Use the complimentary Middletown Mural Map to locate each vibrant artwork. Try to find all 14 on your self-guided walking tour for some fun and beauty as you uncover the storybook charm of downtown.

Tour the Governor’s House

Listed on the National Register of Historic Places, this stately brick Georgian mansion provides a glimpse into 18th century life for Delaware’s upper class and political elite. Built in 1790 by local businessman John Cochran and sold just a year later to three-term Delaware Governor Joshua Clayton, the home remained in the Clayton family for over a century.

Guests can tour the beautifully-preserved period rooms adorned with many original antiques and fixtures owned by the Clayton family. Be sure to explore the gardens and grounds as well. Fun fact – two different U.S. Presidents, George Washington and Thomas Jefferson, were entertained as guests here! Self-guided tours run daily, with guided tours offered on weekends.

Spend a Day at Lums Pond State Park

For outdoor lovers, Lums Pond State Park tops the list of things to do in Middletown. Encompassing 1,790 acres surrounding the largest freshwater pond in Delaware, this state park boasts hiking trails, fishing spots, sporting facilities, and the famous Go Ape treetop adventure course.

Bring your own kayak or canoe to explore the serene pond dotted with small islands – no power boats allowed! Or rent one on-site and spend the day paddling. Anglers can cast a line for popular catches like perch, catfish, and crappies from the fishing pier or along the banks of the pond’s cypress trees and lily pads. With a Nature Center and observation deck for wildlife viewing, visitors to Lums Pond State Park immerse themselves in nature just minutes from Middletown.

Other activities in warmer months include disc golf, archery, and camping. Families also enjoy the large outdoor playground. Grab a snack or ice cream at the seasonal concession stand too!

Bike the Junction and Breakwater Trail

Stretching 6.2 miles between Rehoboth Beach and Lewes, this paved biking and walking trail follows the former rail bed of the historic Junction and Breakwater railroad line. Fully accessible and crossing through wooded areas, marshlands, and farmland, it’s a beautiful route showcasing the varied landscapes of Delaware’s coastal region.

Seven trailheads with parking provide easy access to the Junction and Breakwater Trail, including one in downtown Milton right along Broad Street. From here, it’s a quick drive into Middletown for other adventures before/after your bike ride. Pack a picnic lunch to enjoy along the trail too.

As a relatively flat and straight path on a gravel stone base, the Junction and Breakwater Trail offers an easy excursion for cyclists of all ages and skill levels. Make plans to bike it in both directions out-and-back for a 12.4 mile ride. You’ll be treated to fresh air, exercise, and plenty of natural scenery.

Tour Two Local Wineries

Delaware’s wine industry holds its own with vineyards dotting the landscapes of Kent and Sussex Counties. Two of the state’s best wineries operate tasting rooms right in Middletown, offering visitors a delicious introduction to local vino.

Harvest Ridge Winery occupies a 150-year-old farm along the southern border of Middletown. Its varietal wines earn prestigious awards year after year. Their Harvest Red blend and Chambourcin Reserve rate among the most popular. The Harvest Ridge tasting room provides a cozy, rustic setting to sample six different wines paired with snacks. Outdoors, guests can stroll through the vineyards and lush gardens.

A few miles away lies Pizzadili Winery, also specializing in French hybrid varietals. Guests rave about their sweet fruit wines made from blackberries, blueberries, and peaches harvested fresh from the farm. The tasting room here feels lively and modern. Pull up a seat at the wine bar or lounge on the veranda to sip fantastic local wines while munching on brick-oven pizza. With live music performances many weekends in warmer months, Pizzadili Winery makes an ideal evening outing during a stay in Middletown.

Marvel at Steam Engines at the High Wheeler Antique Power Museum

Located at the entrance of Lums Pond State Park, the High Wheeler Antique Power Museum appeals to visitors of all ages – which makes sense given their tagline boasts “Big Toys for Big Boys!” Spanning three large buildings, the museum showcases a fascinating collection of antique engines, tractors, and machinery from the early 20th century during the transition from steam power to petroleum products.

See operational steam traction engines built in 1915 – some weighing over 25 tons! Watch blacksmithing demos using a 150-year old forge and giant trip hammer machine. Check out vintage trucks and tractors, marvel at early washing machines and butter churns, or view the large Lionel train layout. The museum aims to preserve Delaware’s agricultural history while providing an interactive and educational experience for visitors. Open on weekends from April through October.

Catch a Show at the Everett Theatre

Middletown punches above its weight class when it comes to cultural venues like the Everett Theatre on Main Street. Built in 1940 as a movie house and later home to live vaudeville shows, the charming Art Deco theater fell into disrepair over the decades before undergoing an extensive renovation financed by the state and private donors.

Reopened in 2011, the state-of-the-art Everett Theatre can now host larger Broadway touring productions on its bigger stage along with concerts, comedy shows, film screenings, dance recitals, lectures, children’s theater and more. The upcoming roster promises nationally touring musical acts like The Beach Boys and classic rock bands like Blue Oyster Cult along with tribute bands. Beyond just the impressive marquee and neon lights, the Everett Theatre provides a historic centerpiece and source of community pride right in Middletown’s downtown.

Attend Riverfest

For one glorious weekend each July, Middletown celebrates everything wonderful about small town living at their giant block party known as Riverfest. Drawing over 15,000 people each year, the festival packs in two music stages, a carnival midway with rides and games, model boat regatta, petting zoo, fireworks, and over 100 craft and food vendors.

New events debut each year like the Riverfest Brewfest spotlighting Delaware craft breweries or the anything-that-floats Redneck Yacht Club cardboard regatta. You’ll find all ages entertained with activities like cornhole competitions, eating contests, magic shows, stilt walkers, jugglers, face painting, and inflatable bounce houses…plus the obligatory parade! All made possible by hundreds of community volunteers and centered around “The Town in the Middle”.

Make Plans for M.O.T. Big Ball Marathon Weekend

In early April, the Middletown community proudly hosts the MOT Big Ball Marathon commemorating the town’s history as “The Town in the Middle” situated halfway between Maryland and New Jersey. Offering something for all fitness levels, the MOT Big Ball Marathon weekend features a full marathon, half marathon, 5-miler race and 1-mile fun run.

The certified marathon and half marathon route highlights Middletown’s small-town charm as participants run through the heart of downtown past the sloping Main Street, then journey into scenic surrounding countryside of the Coastal Plain, over gentle rolling hills and past fragrant apple orchards.

Along with athletic challenges and finisher medals for motivation, runners boost community spirit and garner enthusiastic crowds as local bands and color guard groups line Main Street. Spectators can walk to multiple points along Main Street to cheer everyone on during the signature event for this running-loving town.

Play Disc Golf at Silver Lake Park

For affordable outdoor fun close to downtown Middletown, pack up some discs and head to Silver Lake Park to play a round of 18-hole disc golf. The wooded park features oak, cedar and sycamore trees that frame challenging shots along with elevation changes to test your skills.

Located right off Main Street, the free disc golf course takes about an hour to play as you zigzag across small foot bridges and shady hills dotted with benches. Bring your own discs or rent them on-site. Just look for the chain basket targets set up across the park, with tee pads indicating each hole. The PARKS department even offers free lessons.

Open year-round from dawn to dusk, the disc golf course at Silver Lake Park offers beginners and experienced disc throwers an outlet to learn and play while surrounded by the community park’s scenic nature and fun obstacles.

Tour Appoquinimink Friends Meetinghouse

Quaker settlers from Philadelphia and New Jersey established communities along the Delaware River and Bay beginning in the 1650s. Among the oldest houses of worship in Delaware lies the Appoquinimink Friends Meetinghouse located just south of Middletown. Quakers founded this meeting, originally constructed of logs around 1682, and rebuilt with brick on the same site in 1786.

Still an active Quaker meeting today, the historic Appoquinimink Friends Meetinghouse and burying grounds provide visitors a glimpse into 300 years of Delaware Quaker history and culture. Download a free audio walking tour to fully appreciate the grounds, simple architecture, and importance of faith in Middletown’s early days. Visitors are also welcome to attend silent worship services held every Sunday morning.

Go Back in Time at Fort Christina Park

History comes alive at Fort Christina State Park which memorializes the first permanent European settlement in Delaware. Though mistakenly dubbed “Fort Christina”, Swedish settlers actually named their 1638 landing area “Altena” after a castle in their homeland. To protect the fledgling colony from British threats, the Swedes did construct earthen embankments with a wooden blockhouse.

Today Fort Christina State Park preserves the site along the Christina River as an open-air museum. Visitors can explore recreated elements of the Swedish fort including cannon sites, inscribed memorial stones shipped from Sweden, and the historic Old Swedes Church built in 1699. Living history reenactments feature guides dressed in period clothing bringing stories of early Delaware settlements to life. Check event listings for battle reenactments with musket firing demonstrations happening throughout the year!

Conclusion

Blending small town charm with plenty of family fun, Middletown makes an ideal base to explore Delaware’s northern region. Through downtown history, immense state parks, cultural events, and even a bustling wine trail, Middletown truly offers visitors “The Best of Both Worlds” between quaint community and inviting attractions. Use this list of top things to do in Middletown DE to make the most of your upcoming visit!

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