Middletown Travel Guide

If you're planning to visit Middletown in Maryland, our travel guide can help you with everything from places to visit to where to stay, and more.

Introduction to Middletown

Middletown, situated in Frederick County of Maryland, is a charming small town that is surrounded by stunning natural beauty. The town has a rich history and plenty of cultural attractions that make it an ideal destination for every type of traveler. Visitors can enjoy the town’s elegant architecture, scenic views, hiking trails, and cultural events throughout the year.

List of Places to Visit in Middletown

If you’re planning a trip to Middletown, here are some places that you simply cannot miss:

Culturally Important Attractions: Museums and Historical Places

  • Catoctin Furnace: a 19th-century industrial village and one of Maryland’s earliest iron-making industrial sites.
  • South Mountain Battlefield: a Civil War battlefield where Union forces fought back against Confederate troops.
  • Gathland State Park: a National Historic Landmark with a museum that showcases the life and work of War Correspondent George Alfred Townsend, “Gath.”

Natural Attractions of Middletown: Outdoor Adventures and Scenic Views

  • Appalachian Trail: Enjoy hiking through the stunning forested hills of the Appalachian Mountains.
  • Gambrill State Park: A pristine park that provides stunning views, hiking trails, picnic spots, and birdwatching opportunities.
  • Sugarloaf Mountain: A popular destination for hikers and rock climbers due to its stunning views of the surrounding area.

Hiking/Biking Routes of Middletown

One of the most exciting ways to experience the natural beauty of Middletown is through hiking and biking. Here are some of the best routes to take:

  • Appalachian Trail: Hiking the southern half of the trail from Annapolis Rock to the Mason-Dixon Line is a popular choice.
  • Catoctin National Recreation Trail: Running for 8.6 miles, the trail takes hikers and bikers through Catoctin Mountain Park.
  • Middletown Heritage Trail: This leisurely trail is perfect for families and history buffs as it allows visitors to explore the highlights of Middletown’s history.

Best Things to Do in Middletown: Activities and Tours

Apart from hiking and biking through Middletown’s natural beauty, here are some other exciting activities to do in town:

  • Visiting nearby wineries and vineyards: Middletown is in the heart of Maryland wine country, making it a perfect destination for wine lovers. Frederick Wine Trail is a popular choice for tourists.
  • Take a walk through the historic downtown: The town has a rich history that is reflected in its architecture. Walking down the streets of the historic district is worth it.
  • Enjoy cultural events: Middletown hosts several cultural events throughout the year, from historical reenactments to festivals.

Week-Long Itinerary for Middletown

If you’re planning to spend a week in Middletown, here’s how you can plan your itinerary:

Day Activities
Day 1 Explore downtown Middletown, enjoy lunch at one of the local eateries, visit the Catoctin Furnace.
Day 2 Hike the Appalachian Trail starting at the Annapolis Rock, visit the nearby vineyards.
Day 3 Visit the South Mountain Battlefield, have a picnic at the Gathland State Park.
Day 4 Visit Frederick City and the National Museum of Civil War Medicine.
Day 5 Hike the Catoctin Recreation Trail, visit the Cunningham Falls State Park.
Day 6 Visit Sugarloaf Mountain, enjoy lunch at nearby wineries.
Day 7 Take a break, relax, and enjoy the scenery. You’ve earned it!

Food and Drink Scene of Middletown

Middletown has plenty of options for foodies who want to taste the local cuisine:

Must-Try Dishes

  • Crab cakes: Since Middletown is in Maryland, it’s a must-try dish!
  • Sour beef and dumplings: A German dish that is a highlight of Maryland’s culinary history and food culture.
  • Chicken Chesapeake: A dish made of chicken topped with crab meat.

Local Beverages

  • Maryland craft beer: The craft beer scene in Middletown is growing, with several breweries offering a variety of craft beer options.
  • Maryland wines: Visit one of the many vineyards in the area to enjoy a glass of local wine.

Where to Stay in Middletown: Hotels, Hostels, and Guesthouses

Middletown has several options when it comes to accommodation, whether you’re looking for budget-friendly options or luxury hotels.

  • Hampton Inn Frederick: A budget-friendly option located only 3.6 miles from Middletown.
  • Mainstay Suites: This hotel offers extended stay options and is also pet-friendly.
  • The Inn at Stone Manor: A luxurious mansion that offers a relaxing stay with stunning views.

What to Buy in Middletown: Souvenirs and Local Products to Bring Home

Middletown has several stores and shops where you can buy souvenirs and local products. Here are some options:

  • Middletown Valley Historical Society Museum Store: Offers unique historical items and books, art, and paintings that celebrate Middletown’s history.
  • Mountain View Candle Works: Offers handmade candles that make for great souvenirs.
  • Catoctin Breeze Vineyard Store: Offers local wines that you can take back home.

Local Culture and Customs of Middletown

Middletown is a small town with a rich history and legacy, and its cultural customs reflect that. Visitors are expected to be respectful of the town’s customs and traditions.

Best Time to Visit Middletown

The best time to visit Middletown is during the fall, from September to November. The fall season offers the perfect weather for outdoor activities, as well as stunning fall foliage. Spring (March to May) is also a great time to visit as the weather is perfect for hiking and biking.

Do’s and Don’ts of Middletown

Here are some things to keep in mind when visiting Middletown:


  • Respect the historic architecture of the town.
  • Explore the local wineries and vineyards.
  • Take hikes on the many trails available.


  • Don’t litter and maintain the ecological balance.
  • Don’t be disruptive at cultural events.
  • Don’t be disrespectful to the town’s customs and traditions.

Safety and Health

Safety in Middletown

Middletown is generally a safe town, with a low crime rate. However, visitors should still stay aware of their surroundings and belongings.

Health in Middletown

Middletown has several hospitals and clinics that can provide medical attention if necessary. Visitors should also be aware of ticks and wear bug repellent when hiking.

Getting to Middletown: Transportation Options and Logistics

Airports Near Middletown

The closest airport to Middletown is the Hagerstown Regional Airport, located around 40 minutes away from the town.

Bus Stations Near Middletown

Frederick Transit provides bus service to and from Middletown. The nearest bus station is located in downtown Frederick.

Other Options

Middletown is a small town, and the best way to experience it is by driving. Visitors are advised to rent a car if they are not driving their vehicles.

How to Get Around in Middletown

The best way to get around in Middletown is by car. However, visitors can also take a taxi service.

Where to Go Next from Middletown: Nearby Destinations and Excursions

Middletown is a great starting point for exploring other nearby destinations in Maryland, including:

  • Baltimore: A vibrant city with several cultural attractions, shopping districts, and the iconic Inner Harbor.
  • Annapolis: Capital of Maryland, with plenty of historic sites, shopping, and dining options.
  • Washington DC: The political capital of the United States, with historic landmarks, museums, and monuments.


Middletown is a hidden gem that is perfect for those who want to explore Maryland’s natural beauty and vibrant history. With several cultural and natural attractions, visitors can enjoy the best of the town throughout the year. Whether you’re a history buff, an adventure lover, or a foodie, Middletown has something for everyone.