Main Street Middletown, Maryland, has an itinerary for everyone. From a day trip to a romantic weekend, we have curated experiences just for you!
Enjoy a Day with the Ladies
Gather the ladies for a much-needed day of relaxation and self-care. Book a facial at Bug and Jane and luxuriate in signature skin care treatments. Need to bring the kids? No problem, they can nap in the stroller during your visit. When it’s time for lunch, treat yourself to housemade Greek specialties at Alekos Village Café or all-American classics at Main Cup, a local staple.
After lunch, head down the street and enjoy a bit of shopping at the charming Turquoise Trailer or Hello Gorgeous Boutique. Finally, drop by the Cry Baby Café & Toy Library and enjoy a locally sourced coffee and bakery treat! Kids can enjoy the toy library while you catch up with your friends.
Plan a Day with the Family
Spend a day with the family in Middletown! Start your outing with a hearty breakfast at Dempsey’s Grille before exploring nature in one of our beautiful parks. Hike, bike, or horseback ride on 16 miles of trails in Gambrill State Park. Continue to surround yourself with nature at Valley-HomeMade and HomeGrown, as many weekends the farm is open for pick-your-own flowers and families are welcomed to picnic here.
No family trip is complete without ice cream! Stop in at the charming More Ice Cream and enjoy frosty treats on the wrap-around porch, or check out LDS Café, the oldest licensed purveyor of Hershey’s Ice Cream, offering sundaes, floats, and soft serve ice cream.
Ice cream is a Middletown mainstay, so taste your way through our Ice Cream Trail ─ brochures are available at the Welcome Center, so you won’t miss a shop!
Couples Retreat
Spend a weekend with someone special in Middletown. The town is home to several charming Airbnbs ─ but reserve early, as they book quickly. Spend the day walking hand-in-hand along our Main Street, enjoying one or all of our Heritage Walking Tours.
Information can be found at the Middletown Welcome Center. Make sure to save enough time to visit the region’s local wineries, and the not-to-be-missed Orchid Cellars, Maryland’s first meadery.
Middletown is home to several one-of-a-kind restaurants, perfect for a date-night dinner. Make a reservation at The Main Cup, Aleko’s, or Fratelli’s, and savor big taste in a small town. After a restful evening, kickstart the morning with coffee and breakfast at Beans & Dreams. One energized, take in the fresh mountain air by hiking the Appalachian Trail, just a few miles west of downtown, and fuel up at Tapia’s on Main for Sunday brunch before returning home.
Whether you need a quick getaway with friends, family, or that special someone, Main Street Middletown, Maryland provides charm, history, delicious food, wineries, and more for a memory-making day trip or weekend.
Plan your visit to Main Street Middletown today ─ Where Charm and History Meet!
Feature image courtesy Mike Tranchitella
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