Thanks to so many Vintage Vehicle owners and visitors who came to our 2nd Annual Vintage Vehicles in the Valley event!  We hope everyone had just as much fun as we did and we look forward to seeing everyone this year on June 13, 2020! 



Vintage Vehicles in the Valley

Take a walk down memory lane with Main Street Middletown as we host our 3rd Vintage Vehicles in the Valley event!  Bring the whole family – all three or even four generations can all enjoy the afternoon looking at antique cars, hot-rods, motorbikes, and more!  

Relax and take in the music performed live by Simple Pleasure, bringing back the best cruising songs of the 1950s, 1960s, and 70s!  Enjoy specialty snacks from Randy’s Candy’s ( including serving up the original fruit flavored colas, like the NeHi, and Baltimore-original, Frosty Blue Cream soda!  Other food offerings will be from local favorite, Carroll Concessions with the classic dogs, brats, burgers, and fries and Wood Fire Pizza by Pizza Llama!  Be sure to participate in the 50/50 raffles and attendees get to vote on Best in Show! 

Don’t be surprised if you see a few poodle skirts sashaying around town – and you are welcome to come donned in period clothing to add fun and flare to our event! 

Proceeds from this event go to support two worthwhile causes:  Warrior Canine Connection and Main Street Middletown, specifically our efforts to restore two historic buildings.  

Vintage Vehicles in the Valley is the perfect opportunity to browse downtown Middletown, relax, have fun, all while supporting two great causes.    

For Visitors – plenty of parking will be available at the Elm Street Parking lot (located between Dempsey’s Grille at 116 West Main Street and Boggs Environmental at 200 West Main Street). 

For vendors – does this sound like your target market?  We are looking for vendors who can offer cool car collectibles, memorabilia, car services and parts that will enhance this event!  Please click here to complete a Vendor Application. 

For Car Owners – The more the merrier! 

  • We are encouraging Early-Bird registration with Dash Plaques for the first 100 registrants! 
  • Seven award categories including: Best in Show, Best Stock Automobile, Best Modified Automobile, Best Specialty Vehicle, Best Stock Truck, Best Modified Truck, and Best Motorcycles.
  • Black-top parking and overflow on manicured grass parking areas
  • $15 Registration Fee (registration below)  

On-site registration will be available from 9am to 11am, Saturday, June 8th.  Please enter West Green Street from MD 17/North Church Street.  Our friendly volunteers will assist you at the registration table and parking attendants will direct you to park. 

Register your vehicle!


First Name*

Last Name*




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There's a $15 Vehicle Registration fee. Once you submit this form, you'll be taken to PayPal to complete your payment.

Third Annual Vintage Vehicles in the Valley


June 13, 2020


8:30 am – 11:00 am


11:30 am – 2:30 pm


Town Hall

31 West Main Street 

Middletown, Maryland 21769