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Looking for a charming small-town getaway in scenic Maryland? Head to Middletown! Nestled in the heart of the Middletown Valley and surrounded by the Catoctin Mountains, Middletown offers historic charm, outdoor recreation, and easy access to Civil War landmarks and nearby wineries. It’s a peaceful base for exploring western Maryland’s countryside and heritage.

Middletown, MD Highlights:

  • For History Buffs: Walk the Middletown Historic District – Explore 19th-century architecture, churches, and Civil War history along Main Street.
  • For Nature Lovers: Hike in Gambrill State Park – Enjoy wooded trails, mountain overlooks, and picnic areas just minutes away.
  • For Families: Visit South Mountain Creamery – Tour a working dairy farm, bottle-feed calves, and enjoy homemade ice cream.
  • For Wine Enthusiasts: Sip at Orchid Cellar Meadery & Winery – Try handcrafted meads and wines in a rustic hillside setting.
  • For Golfers: Play at Maryland National Golf Club – A scenic, challenging course nestled in rolling countryside with stunning views.

🌤 When I like to visit Middletown, MD

The best time to visit Middletown is in the spring and fall (April–June and September–October). These seasons bring comfortable temperatures, colorful foliage or blossoms, and excellent conditions for hiking, sightseeing, and wine tasting. Summers are warm and lively, while winters are quieter and great for cozy getaways.

🗺 My tips for getting to Middletown, MD

  • By Car: Middletown is located on U.S. Route 40 Alternate, about 10 minutes west of Frederick and 1 hour from both Baltimore and Washington, D.C.
  • By Train: The MARC Train (Brunswick Line) serves nearby Frederick; you can take a short drive or rideshare to Middletown.
  • By Plane: Fly into Baltimore/Washington International (BWI) or Dulles International (IAD) airports and rent a car.

🏬 Where I like to stay in Middletown, MD

  • Recommended for Couples: Inn BoonsBoro (nearby) – Luxurious literary-themed rooms in a historic inn owned by author Nora Roberts in nearby Boonsboro.
  • For Families: Frederick Inn Bed and Breakfast – Spacious, family-friendly accommodations in a restored Victorian home just a few miles away.
  • For Convenience: Hampton Inn Frederick – Reliable hotel chain close to Middletown, with modern amenities and easy highway access.

😍 Best Things to Do in Middletown, MD

1. Washington Monument State Park


"Hike scenic trails and see historic views on a peaceful, affordable outdoor trip."
- VI

Washington Monument State Park

© Washington County Government - Maryland

  • Where is Washington Monument State Park located?
  • Why was Washington Monument State Park created?
    • The park was created to preserve the Washington Monument, a 40-foot-tall tower that honors George Washington, the first President of the United States.
  • Where is the monument located?
    • The monument is situated near the summit of South Mountain's Monument Knob.
  • When was the original Washington Monument built?
    • The original tower was built in 1827 and was the first monument dedicated to George Washington.
  • How was the monument originally constructed?
    • The monument was constructed as a dry-laid stone tower and was built on July 4, 1827 by the citizens of Boonsboro.
  • What happened to the original monument?
    • The site was a popular meeting place for Boonsboro residents, but over time, weather and vandalism led to its destruction.
  • When was the monument site purchased and restored?
    • In 1920, the Washington County Historical Society bought the one-acre site and later deeded it to the state to be used as a park.
  • How was the monument rebuilt?
    • The tower was rebuilt in its current form, incorporating the original cornerstone and a copy of the original dedication tablet.

6620 Zittlestown Rd, Middletown, MD 21769, Phone: 301-791-4767

2. South Mountain Creamery


💕 "Meet farm animals and enjoy fresh ice cream on a fun, family-friendly visit."
- VI

South Mountain Creamery

© South Mountain Creamery

  • What is South Mountain Creamery?
    • South Mountain Creamery is a dairy farm near Middletown, Maryland, where they raise their own cows, bottle their own milk, and make their own butter, yogurt, and ice cream.
  • What makes South Mountain Creamery unique?
    • The farm provides home delivery, a service rarely offered today, bringing fresh dairy products straight to customers' doors.
  • How can customers order from South Mountain Creamery?
    • Customers in the area can use the online farmers' market to order milk and dairy products for home delivery.
  • How large is South Mountain Creamery’s delivery network?
    • The farm is the largest home delivery business in the region, working with almost 200 local sustainable farm families and serving over 9,000 families.
  • What other products does South Mountain Creamery offer?
    • In addition to dairy, meat, and eggs, they also sell local and organic produce, baked goods, nut butters, salsa, homemade soups, salads, healthy snacks, and slow-cooker meals.

8305 Bolivar Rd, Middletown, MD 21769, Phone: 844-762-6455

3. Willow Oaks


I like: "Shop artisan goods and explore native plants on a relaxing, unusual countryside stop."
- VI

Willow Oaks

© Willow Oaks

  • What is Willow Oaks?
    • Willow Oaks is a small certified organic farmhouse-style cidery established in 2013, located on a 35-acre farm in Middletown, Maryland.
  • Who owns Willow Oaks?
    • The cidery is owned by Eric Rice and Lori Leitzel Rice, who craft their ciders using certified organic ingredients.
  • What kinds of apples are used in Willow Oaks cider?
    • Their cider is made from about 20 varieties of certified organic American heirloom apples.
  • What other fruits are added to Willow Oaks ciders?
    • They enhance their ciders with organic pears, blueberries, black currants, and other fruits for unique flavors.
  • What is special about the farm where Willow Oaks is located?
    • Their farm, Country Pleasures Farm, is the oldest organic farm in Maryland.
  • How much cider does Willow Oaks produce each year?
    • Willow Oaks produces only about 2,500 gallons per year, making their ciders a rare local specialty.
  • Where can you buy Willow Oaks ciders?
    • Most of their ciders are available only at their tasting room in Middletown, Maryland.
  • What is the experience like at the Willow Oaks tasting room?
    • The tasting room is a pleasant, charming local hangout where both locals and visitors can enjoy different kinds of cider and have a relaxing conversation.

6219 Harley Rd, Middletown, MD, Phone: 301-371-4814

Unique Attractions

4. Mazzaroth Vineyard


"Taste small-lot wines and admire vineyard views on a quiet, romantic afternoon outing."
- VI

Mazzaroth Vineyard

© Mazzaroth Vineyard

  • What is Mazzaroth Vineyard?
    • Mazzaroth Vineyard is a wine vineyard located in Middletown, Maryland, in the southwestern part of Frederick County.
  • When was Mazzaroth Vineyard established?
    • The vineyard was initially planted in 2011, with a one-quarter-acre test vineyard added in April 2012. It has been growing ever since.
  • How large is Mazzaroth Vineyard?
    • The vineyard has expanded over the years and currently occupies 1.75 acres.
  • What is the mission of Mazzaroth Vineyard?
    • Mazzaroth’s mission is to grow high-quality wine grapes within the Catoctin American Viticultural Area (AVA).
  • Where is the Catoctin American Viticultural Area (AVA) located?
    • This AVA stretches from Braddock Mountain to the Potomac River and South Mountain, making it a prime region for grape growing.
  • Where can you buy Mazzaroth wines?
    • Mazzaroth wines are available at many bars, restaurants, and liquor stores in and around Frederick County.
  • Can visitors tour Mazzaroth Vineyard?
    • The vineyard and winery are closed to new visitors and open only by appointment for case-club members and those holding Mazzaroth Vineyard gift cards or certificates for complimentary tastings.

8333 Myersville Rd, Middletown, MD 21769, Phone: 301-639-0303

5. Maryland National Golf Club


Among my top 5: "Play a challenging round and enjoy scenic fairways on a relaxing golf getaway."
- VI

Maryland National Golf Club

© Maryland National Golf Club

  • What is Maryland National Golf Club?
  • Who designed Maryland National Golf Club?
    • The course was designed by world-renowned architect Arthur Hills, who incorporated the area's dramatic terrain and wetlands into the layout.
  • What kind of challenges does the course offer?
    • The 6,811-yard course features rolling fairways, holes carved out of natural wooded terrain, and various water hazards, ensuring a unique challenge on each hole.
  • What are the scenic features of Maryland National Golf Club?
    • Nestled in the rolling hills of central Maryland, the course offers spectacular views of the Catoctin Mountains.
  • Where is the clubhouse located?
    • The clubhouse is situated at the highest point on the property, overlooking the 18th hole and offering panoramic views of almost every part of the course.
  • What amenities does Maryland National Golf Club offer?
    • The club features a full-service golf shop, a tavern, corporate meeting spaces, and locker rooms.

8836 Hollow Rd, Middletown, MD 21769, Phone: 301-371-0000

🥗 Where to Eat in Middletown, MD

  • Recommended for Casual Fare: The Main Cup – Cozy café and restaurant serving American classics, craft beer, and local wines.
  • For Pizza & Italian: Fratelli's New York Pizza – Family-run spot known for hearty portions and friendly service.
  • For Brunch or Bakery Treats: Beans in the Belfry (Brunswick) – Quirky café set in a restored church with coffee, sandwiches, and pastries nearby.

🎟 If you are interested in local events:

  • For History Lovers: South Mountain Heritage Days (September) – Guided hikes, reenactments, and family-friendly activities celebrate the area's Civil War past.
  • For Community Fun: Middletown Heritage Festival (Fall) – Parade, crafts, food vendors, and live entertainment in the heart of town.
  • For Holiday Cheer: Christmas in the Valley (December) – Tree lighting, visits with Santa, and small-town seasonal spirit.

Day Trip Itineraries Within 30 Minutes of Middletown, MD:

  • For Urban Exploration: Frederick (15 min) – Browse galleries, dine along Carroll Creek, and tour historic homes and museums.
  • For Civil War History: Antietam National Battlefield (25 min) – Walk solemn trails and learn about one of the war’s most significant battles.
  • For Hiking & Views: Appalachian Trail at South Mountain (10–15 min) – Hike short or long sections with panoramic valley views.
  • For Family Fun: Catoctin Wildlife Preserve (25–30 min) – See exotic animals, feed safari creatures, and enjoy kid-friendly experiences.
  • For Farm & Fruit Picking: Scenic View Orchards (15 min) – Seasonal berries, apples, and produce with beautiful views of the valley.

📔 I get asked this a lot so I decided to include it:

  • Where is Middletown, Maryland located?
    • Middletown is a small town in Frederick County, Maryland, situated in the Middletown Valley, which stretches between the Catoctin Mountains and South Mountain.
  • What is Washington Monument State Park?
    • Located near Middletown, Washington Monument State Park was created to preserve the Washington Monument, a 40-foot-tall tower built to honor George Washington.
  • What is South Mountain Creamery?
    • South Mountain Creamery is a dairy farm and the largest home delivery business in the area, partnering with nearly 200 local sustainable farm families.
  • What is Willow Oaks?
    • Willow Oaks is a small certified organic farmhouse-style cidery, located on a 35-acre farm near Middletown.
  • What is Mazzaroth Vineyard?
    • Mazzaroth Vineyard is known for growing high-quality wine grapes in the Catoctin American Viticultural Area.

At a Glance:


Best Time to Visit Places to Stay Tips for Visiting
Spring (March-May) – Mild temperatures and blooming countryside, ideal for scenic drives and outdoor activities. Inn at Red Horse Farm – A charming bed & breakfast offering a quiet retreat. Explore South Mountain State Park – Hike historic trails and enjoy beautiful views.
Summer (June-August) – Warm weather perfect for vineyard visits, hiking, and small-town festivals. Hampton Inn Frederick – Comfortable accommodations just a short drive from Middletown. Visit Orchid Cellar Meadery & Winery – Enjoy locally crafted meads and wines in a scenic setting.
Fall (September-November) – Cool temperatures and stunning fall foliage, great for historic tours and apple picking. Homewood Suites by Hilton Frederick – Spacious suites with easy access to local attractions. Drive the Middletown Valley Scenic Byway – Take in vibrant autumn colors and rolling hills.
Winter (December-February) – Cozy, festive atmosphere perfect for holiday events and quiet retreats. Town Hill Bed & Breakfast – A relaxing countryside stay with a historic touch. Explore downtown Middletown – Discover local shops, cafés, and historical landmarks.

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