12 Attractions in Middletown, Delaware

Last Updated on March 3, 2024 by Emily Johnson

Middletown is a charming small town in central Delaware, located about halfway between Wilmington and Dover. With its historic downtown, attractive parks and gardens, and family-friendly attractions, Middletown makes a great weekend getaway or day trip destination from anywhere in the Delaware/Maryland/Pennsylvania area.

This article outlines 12 of the top attractions that you’ll want to include on your Middletown itinerary, from museums and performing arts to historic sites, recreation, shopping, and dining. With something for visitors of all ages and interests, Middletown has plenty to see and do for a fun-filled day or two.

Historic Downtown District

Downtown Middletown transports you back in time with its historic 18th and 19th century buildings housing cute boutiques, cafes, restaurants, and galleries. The downtown district covers about ten square blocks centered on Broad and Main streets, with over 60 contributing properties that are listed on the National Register of Historic Places.

Must-see landmarks here include the Old Town Hall, built in 1856 and now home to the Middletown Historical Society Museum. The society offers guided walking tours for visitors to explore downtown and learn about the architecture and history of this charming river port town.

Also be sure to check out the Victorian-era Johnson Building with an ornate brick façade. The three-story building was constructed in 1886 and today houses shops and eateries like Sweet Lucy’s Ice Cream Parlor. Don’t miss strolling down quaint Lake Street, lined with colorful Victorian homes dating back as far as the 1830s.

Johnson Victrola Museum

Located in the historic downtown district, the Johnson Victrola Museum celebrates Middletown native Eldridge Johnson’s pioneering innovations in the early phonograph industry. The museum’s collection includes over 100 antique Victrolas manufactured by Johnson’s Victor Talking Machine Company between 1901 and 1929.

This fascinating museum lets you discover how the technology evolved from purely mechanical cranked models to advanced electric record players. Especially impressive is the ornate 1927 VV-XIV “Credenza” model, which sold for a whopping $275 when average annual wages were under $1,400. Make sure to view the 15-minute video chronicling the history of the company Johnson founded right here in his hometown of Middletown.

Kalmar Nyckel

Docked along the winding Smyrna River, the Tall Ship Kalmar Nyckel is an impressive re-creation of the ship that brought the earliest permanent European settlers from Sweden to Delaware in 1638. Tours aboard the docked ship bring Delaware’s founding history alive, from the cramped steerage accommodations to cargo areas brimming with period goods.

For an additional charge, visitors can choose from various sailing trips into the Delaware Bay and River. Options range from two-hour day sails to three-day “Summer Camp Afloat” adventures including wildlife viewing, fishing, and kayaking along the coast. Check the calendar in advance for festival days with historical reenactments, pirate invasions, music, and more family fun.

Middletown Historic District

In addition to the downtown area, Middletown also boasts a larger 210-acre historic district showcasing over 300 historic homes spanning three centuries of changing architectural tastes. The district lies along both sides of main street (Route 301) heading north from downtown Middletown.

Here you can view various fine examples of buildings in styles from simple Early American to mid-19th century Gothic Revival and Italianate Victorians, up through stately early 20th century Colonial Revival manors. Homes here were built and owned by successful Middletown businessmen, shipbuilders, merchants, and farmers over its long history.

Those staying overnight can choose from cozy vintage bed and breakfast accommodations, like the Everett House built in 1836 or Amos House from 1860. Guided trolley tours from downtown allow visitors to take in the full scope of Middletown’s remarkably well-preserved historic residential district.

Appoquinimink Friends Meetinghouse and Cemetery

Just south of Middletown’s main historic district sits the Appoquinimink Friends Meetinghouse, a tranquil site providing a vivid look into Middletown’s early Quaker history. The current meetinghouse structure dates to 1788 with many older headstones dotting the grounds, some dating as far back as the early 18th century.

Quaker settlers fleeing persecution in Europe founded Middletown in 1680 on lands purchased from the indigenous tribe whose name lent itself to the Appoquinimink River bordering the town. In addition to the historic building and cemetery, visitors can view the on-site museum with its artifacts and records documenting over three centuries of continuous Quaker history anchored to this serene spot.

Silver Lake Park

Covering over 100 scenic acres in central Middletown, Silver Lake Park provides a variety of recreational fun for families and outdoor enthusiasts. Highlights include a tranquil 25-acre millpond, pedal boating and kayaking rentals, fishing areas, picnic sites, playgrounds, ball fields, biking and hiking trails.

The local garden club also maintains several delightfully designed themed garden areas around the central lake and along the trails, like the blue Hen children’s garden, butterfly garden, heritage herb garden and veterans memorial garden. Seasonal amenities include community theater productions in the park amphitheater on summer evenings.

Middletown Arts Center

Located in downtown Middletown’s historic district, this multi-use facility serves as the community’s prime venue for quality performing and visual arts. The Crown Theater auditorium seats 500 and hosts concerts, theater productions, dance recitals, children’s theater, film screenings, lectures and other events year-round.

The Everett Theater wing accommodates smaller-scale productions, recitals, receptions, meetings and classes. Gallery exhibits feature works by regional visual artists, with openings coordinated with the downtown Friday art loop events. Check their online calendar for the full schedule of entertainment and cultural enrichment opportunities right at the hub of historic Middletown.

Vesty Recreation Center

For indoor sports and recreation, the Middletown Vesty Recreation Center can’t be beat. The facilities include multiple hardwood basketball courts, a roller hockey rink, and volleyball courts available for drop in play. The center also offers free play times as well as organized team leagues for youth and adults.

Kids will particularly enjoy the large jungle gym style playground structure known as the “orange monster” with its multicolored tubes and tunnels. Birthday party packages are available covering private use of select areas along with amenities like invitations, food and supervision. Check the online calendar for open gym times, league schedules, and special events.

Paradise Farms Campground

Nature lovers will appreciate camping amenities tucked just north of Middletown at Paradise Farms. Tent and RV campers can enjoy peaceful surroundings with 150 wooded and open sites all providing free wireless internet access.

Recreational facilities include a modern bathhouse, jumping pillow, mini golf course, game room, snack bar and both adult and kiddie swimming pools. Planned activities run the gamut from ceramics painting to scavenger hunts, magic shows to tie dye t-shirt making. Paradise Farms conveniently sits right on the route 5 bus line for easy access to downtown shops and restaurants just 2.5 miles south in Middletown.

Cantwell’s Tavern

No visit to Middletown would be complete without stopping at historic Cantwell’s Tavern, found along downtown’s High Street since 1824. Now run by the third generation of Cantwell family owners, the restaurant proudly maintains its 19th century ambiance of hand hewn beams and brick archways.

Start your visit at the dark wood bar, lit by gas lanterns and packed with quirky curios lining the walls and rafters. Then move into the adjacent dining rooms and courtyard for menu highlights like homemade crab cakes, prime rib and Cantwell’s signature sticky toffee pudding. Just save room for one more pint of ale at the bar before you leave this landmark Middletown eatery.

When you work up an appetite strolling and shopping the district, choices abound for a meal or snack along Main Street and side roads like Broad and Lake. Bright awnings will lure you into bakeries, coffee shops, sandwich delis, pubs, and upscale American fare at restaurants like Cool Springs Cafe, The Double L Diner or Verano Italian.

Boyd’s BookBinder Gallery

Tucked away on scenic Cochran Street lies a real hidden gem for book lovers and those who appreciate masterful craftsmanship. Inside his historic Greek revival home, master bookbinder Craig Boyd transforms new printed pages into stunning leather-bound volumes. His onsite gallery displays samples of over 35 years worth of work, from delicate gold leaf accents to carved dragon reliefs.

The gallery likewise showcases other regional artisans’ works like handmade jewelry, ceramics and turned wood pieces. Beyond the regular merchandise, many of Boyd’s pieces are specially commissioned as cherished gifts marking monumental life occasions. Even if you leave empty handed, you’re sure to depart this little gallery space feeling inspired by traditional handicrafts elevated to fine art form.

Middletown Air Field (MOT)

If touring by private plane, visitors can aim for the Middletown Air Field public use airport, MOT. Their single 2,791 foot paved runway serves up to 20 small aircraft movements daily. Though unstaffed, self-serve fuel is available 24 hours along with lodging and dining options conveniently close to downtown Middletown.

Due to frequent operations by police helicopters and other governmental agencies, pilots are advised to take standard precautions before landing. But on calm wind days with good visibility, expect a smooth arrival to a welcoming grassroots airport serving aviation enthusiasts throughout the Mid-Atlantic since 1941.

Conclusion

With such a remarkable range of historic sites, cultural attractions, recreational facilities, shops and eateries, Middletown truly offers an ideal weekend escape or day trip destination. Conveniently located midway between Baltimore and Philadelphia, this charming Delaware town packs plenty to see and do into its compact half dozen square miles centered around the Appoquinimink River.

The 12 attractions covered here let you soak in over three centuries worth of living history. At the same time, 21st century diversions like live theater, music, visual arts studios, and small business retail promise dynamic entertainment. Outdoor enthusiasts will find boating excursions, riverside camping, biking trails, fishing holes and scenic gardens awaiting exploration.

Whether you crave culture, nature, shopping, dining or historic sightseeing, Middletown serves it all up in walkable easily navigable portions. Indeed this unspoiled river town seems to practically vibrate with echoes of the past while actively looking ahead to a creatively thriving future. Use this guide to discover your own favorite of the many attractions showcasing the very best of Middletown, Delaware.

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