15 Best Things to Do in Middletown, DE

Middletown, DE
Alexanderphoto7 / Shutterstock.com

Middletown, Delaware, got its name from its historical 18th-century location, right in the middle of a trade route called “Herman’s Cart Road.”

Stretching from the Bohemia River to the Cantwell’s Bridge village, this road was the shortest path from the Atlantic Ocean to the Chesapeake Bay.

In 1675, Adam Peterson bought 200 acres of land, a portion of which became the town of Middletown.

When Peterson died, his widow married the Irishman David Witherspoon.

They settled along the King’s Highway, at the crossroads known first as Mr. Blackston’s Corner.

Then, Witherspoon built a tavern that became a popular rest stop for travelers plying the Upper King’s Road.

Some parts of the tavern walls are still inside the walls of today’s Witherspoon Tavern, including the cornerstone, which remains where the builders put it.

Middletown is also the first town in Delaware to put up a monument to the fallen soldiers in World War I.

You can find this at Cochran Square, in the middle of town.

Today, Middletown is a thriving American town and is one of the state’s fastest-growing places.

It’s a great place to live and a terrific place to visit.

Do you want to know more about Middletown, DE?

Here’s a list of the best things to do in town:

See a Show at the Everett Theatre

Exterior of the Everett Theatre with a blue pickup car parked out front.
Alexanderphoto7 / Shutterstock.com

If you’re a fan of the Robin Williams movie Dead Poets Society, you might be familiar with the Everett Theatre.

The 1989 movie filmed several scenes in the theater, including the pivotal performance of “A Midsummer’s Night Dream,” cementing its place in film history.

However, Everett’s history starts earlier than that.

The Everett Theatre opened in 1922, replacing the burned-down Middletown Opera House.

The Everett theatre name sign written in green.
Alexanderphoto7 / Shutterstock.com

Renowned theater architects W.H. Hoffman and Paul J. Henon, Jr. designed the new theater.

Since its debut in Middletown, the Everett has become a popular spot for everyone in the area to catch the latest motion picture or vaudeville performances.

The Everett Theatre still screens films, stages live theater productions and hosts art exhibitions.

Your visit to Middletown won’t be complete without stopping by here.

Spend the Day at the Charles E. Price Memorial Park

Located at Levels Road, the Charles E. Price Memorial Park is a 100-acre property sitting in the heart of gorgeous farmland.

You can take a stroll along the walking trails or check out the vast eight-acre pond.

This pond also carries a pier where you can fish.

Bring your dog and let them run around the park’s fenced-in dog play areas, one of which is for large dogs while the other is for small ones.

The five-acre play area for big dogs also lets you take off their leashes.

Birdwatching is also a popular activity here, so bring your binoculars and spot the waterfowl.

Otherwise, you’ll see ducks, snow geese, and Canadian geese, especially when you visit in the fall and winter.

Learn Local History with the Middletown Historical Society

Like many other states in the country, Delaware brims with a rich history and heritage.

Middletown shares in that history, which it shares with the public through the Middletown Historical Society.

They run a museum that houses historical artifacts from the town's early days, along with objects marking significant occasions in US history.

During your visit, you’ll find permanent collections featuring items from the Middletown Academy between 1827 to 1929.

Observe how the Middletown education system evolved, whether public, private, or boarding schools.

The town is also proud of its peach tradition, noting that the peach industry helped grow Middletown into a bustling city.

You’ll trace the history of this industry at another permanent collection.

Feel Real Fear at Frightland

The Travel Channel once named the Frightland Haunted Attractions into its Top 10 Scariest Haunted Attractions in the country.

Even Forbes and Huffington Post concurred, putting Frightland into their own Top 10 lists.

The complex features four haunted houses and a two-mile Haunted Hayride, just two of the scream park’s eight spooky attractions.

Located directly on Route 13 in Middletown, Frightland is less than an hour from major cities like Philadelphia, Pennsylvania, and Baltimore, Maryland.

It’s a top-rated attraction, so you might need to book tickets before you visit.

Explore the Outdoors at the Silver Lake Park

Visit Middletown village to reach Silver Lake Park, a peaceful and charming property perfect for outdoor escapades.

You can play various sports there, such as basketball, soccer, tennis, and track.

Likewise, the park offers a swimming pool if you want to beat the heat.

Adventurous guests can also bring their boards to the skate park.

Otherwise, just walk along the trails winding around the park.

Check Out Local Artwork at the Gibby Center for the Arts

The Gibby Center for the Arts takes its name from a local Middletown Artist, Gilbert W. Perry.

Since its opening in 2006, the center has enabled local artists of all ages to express themselves through art.

Likewise, the center invites others who might have artistic leanings to attend Gibby’s art classes, exhibits, workshops, and performances.

You can also apply to join the Members’ Guild, and you don’t even need to be an artist to join.

Members also receive many benefits, such as a 10% discount on all classes and workshops.

They also receive invitations to receptions and special events.

Likewise, artists get open studio time and the chance to have their works displayed in the Gibby Gift Shoppe.

Grab Fresh Fruits and Veggies at Filasky’s Produce

For the past 22 years, Filasky’s Produce has become synonymous with Middletown farming.

People buy ingredients at Filasky’s because they cultivate their farms and sell produce straight from these farms.

This process ensures excellent quality fruits and vegetables all year.

You can also visit Filasky’s for leisure.

Go there and join berry-picking activities, and you can even cook your food from the fresh ingredients you bought.

Their track record of farming excellence has led to Filasky’s Produce receiving the Governor’s Agricultural and Urban Conservation Award in 2014.

Stock Up at the Dutch Country Farmers’ Market

Besides fresh produce, the Dutch Country Farmers’ Market also offers hot meals, top-quality furniture, and exciting gifts and services.

You’ll find more than 25 vendors setting up shop there, selling all sorts of things, from baked goods to Amish-made furniture.

You can also buy exotic spices there to freshen up your kitchen repertoire.

After you buy your stuff, head on over to the sit-down restaurant or hop from one food stand to another.

These stalls should let you eat everything that whets your appetite.

Some dishes also appear on special occasions.

For example, you can get the roast pig with mashed potatoes special on the first weekend of every month.

Enjoy the Food at the Metro Pub & Grill

Savor the richness of exceptional Tex-Mex cuisine and wash it down with a glass of ice-cold craft beer at the Metro Pub & Grill, one of Middletown’s bustling restaurants.

They offer a variety of meals, from old favorites nachos and quesadillas to fried catfish po’boys and buffalo chicken flatbread.

Besides craft beers, you can also just go back to the classics like Guinness and the Yuengling Traditional Lager.

The restaurant also serves wines and cocktails if beers aren’t your thing.

Complete your Middletown bar crawl with a glass or two of the Metro’s excellent concoctions.

Prepare for the Holidays at Coleman’s Christmas Tree Farm

Don’t look anywhere else for the finest Christmas trees in the country.

Since 1932, Coleman’s Christmas Tree Farm has offered plenty of unforgettable shopping exercises all year long.

Visit in the summer?

You can enjoy their signature Woodside Farms Handmade Ice Cream.

How about the fall?

You can buy great pumpkins there to spruce up your Halloween celebrations.

However, this 300-acre farm truly shines in the winter.

Visit Coleman’s to get the finest Christmas trees to decorate your home just in time for the holidays.

Besides shopping, Coleman’s also provides school tours and rentals for birthday parties and corporate gatherings.

Roll a Strike at Mid County Lanes and Entertainment

Bring your friends and family to this famous bowling alley in the heart of Middletown.

For example, book a group package and put your bowling skills against your friends to win all-important bragging rights you can treasure forever.

Besides bowling, Mid County Lanes and Entertainment also offers an arcade, where you can play laser tag and air hockey.

There’s even a space for bumper cars.

Introduce your kids to the great sport of bowling, too, while you’re at it.

Catch the Latest Blockbuster at Westown Movies

If you’re in the mood for a popcorn flick, don’t think twice and head right away to Westown Movies, the best digital movie theater in Middletown.

Enjoy a genuinely state-of-the-art moviegoing experience at this theater with 12 screens, including its crown jewel, the GTX Theatre.

Thanks to Westown's excellent acoustics and video quality, the digital screening experience beats other movie theaters in the area by a mile.

Before heading to the theater, you might also want to knock back a few drinks at the bar.

Bring a date or go alone to experience an unforgettable night at the movies.

Get the Full Hibachi Experience at Kiku’s Japanese Steakhouse & Sushi Bar

Middletown's dining options are diverse and offer plenty of unique experiences to the curious guest.

For example, if you haven’t tried hibachi yet, don’t forget to visit Kiku’s Japanese Steakhouse & Sushi Bar in Middletown.

This place should be perfect for Japanese food enthusiasts and great for people willing to try new things.

Get the full hibachi experience at Kiku’s.

Watch the terrific chefs cook your steak right in front of you and taste what makes Japanese cuisine unique.

They also serve fresh sushi and teppanyaki.

For your hibachi meal, you can choose from various meats and fish, such as Angus beef, filet mignon, swordfish, lamb, and salmon.

Other Things to Do Nearby

Revisit Local History at the Corbit-Sharp House

Side view exterior of the Corbit-Sharp house with green trees on the side.
JERRYE & ROY KLOTZ MD, CC BY-SA 3.0, via Wikimedia Commons

Six minutes away from Middletown sits the village of Odessa, another historic place in Delaware.

Once you’re there, make your way to the Corbit-Sharp House, a National Historic Landmark.

It’s also an exquisite example of a home in the Philadelphia-Georgian style.

The house belongs to the annals of United States history because of an encounter between a runaway slave called Sam and an Underground Railroad agent, Daniel Corbit.

A small christmas tree on a circular table, a piano, and a sofa inside the Corbit-Sharp house.
JERRYE & ROY KLOTZ MD, CC BY-SA 3.0, via Wikimedia Commons

Thanks to this record, the National Park Service recognized the Corbit-Sharp House.

The agency included it in the Harriet Tubman Underground Railway Byway and the National Underground Railroad Network to Freedom.

William Corbit built this house in 1774. The Corbits owned the house until 1938 when H. Rodney Sharp bought and restored it.

Today, people consider Sharp the first to undertake historic preservation in Odessa.

Front view exterior of the brick wall and white window building of Corbit-Sharp house.
Ser Amantio di Nicolao, CC BY-SA 4.0, via Wikimedia Commons

Go Back in Time at the Historic Odessa Foundation

Occupying roughly 30 acres of property in the heart of Odessa, the Historic Odessa Foundation hosts various historical landmarks and artifact collections.

Curious tourists in Odessa should visit this place to get the full village experience.

You’ll find a landmark from the moment you step foot inside the grounds.

The Corbit-Sharp House Colonial Revival Garden is a historical landmark, with designs from H. Rodney Sharp and landscape architect Marian Cruger Coffin.

Explore the garden to find heirloom plants cultivated in the 18th century to cure ailments, decorate houses, and season food.

Go deeper to find the historic houses and buildings.

Besides the Corbit-Sharp House, you’ll also find the Wilson-Warner House (ca. 1769), the Collins-Sharp House (ca. 1700), and Cantwell’s Tavern (ca. 1822).

Likewise, the museum houses collections of original furniture taken from Delaware’s famous 18th-century cabinet-makers.

Their collections also include the major regional paintings, prints, textiles, and metals like silver and pewter.

Final Thoughts

Middletown is everything you’re looking for in a small historic town.

It’s got the landmarks, plus the shops and restaurants to fill your bags and bellies in between.

Make Middletown your next weekend getaway.

Book your trip today!