September 2021 – Ask the Experts

Vintage Vehicles in the Valley

September 2021 – Ask the Experts

No matter how you slice it, Frederick County is fabulously fun in the Fall.  And we think Middletown takes the cake when it comes to Celebrating Fall!  Middletown has great places to visit and so many special events that make the most of this time of year.

We admit it, Middletown is awesome all the time, but the scenery in the fall is outstanding.  With the wide blue skies, our varied peaks of our buildings, and South Mountain sloping gently and colorfully in the background sets the stage for all these great activities.

Some advice to enjoy the Fall Fun:

  • Sip wine in the afternoon sun at Orchid Cellars. It’s one of the most relaxing experiences, especially when the views capture so much of the beauty of the fall valley. 
  • Enjoy the view from Tapia’s on Main, from a wonderful array of architectural gems with trees full of fall foliage to looking straight down the National Road to South Mountain.  Need a date night out? How about snuggling up to your significant other as you sit by Tapia’s outdoor fireplace.  
  • Visit a farm! Fall is THE perfect time. One of our favorite fall places — packed with excitement, activity, and iconic fall gourds — is award-winning Jumbo’s Pumpkin Patch. Located on Holter Road, Jumbo’s invites you to pick-your-own pumpkin, play in the corn maze, join a hayride, ride a pony, get your face painted and more.  Jumbo’s Pumpkin Patch is the center of fall family fun in the Middletown Valley!

And more recommendations for you: three major festivals you won’t want to miss this Fall:

  1. Vintage Vehicles in the Valley (September 11) is a super laid-back car show with fantastic cars, trucks, motorcycles, and hotrods spanning almost every decade.  With our love of the National Road, Main Street Middletown sets a pretty stage for custom cars, rarely seen vintage models, prototypes, luxury, sport, and working vehicles all gathered for a good cause!  Proceeds from this event benefit Canine Warrior Connection which pairs a returning service member with a dog as well as the work Main Street Middletown, MD Inc is doing to restore two historic downtown buildings.  Live music evokes those iconic days when we cruised up and down the back roads for the pure joy of driving along with specialty food and drink vendors serving up favorites from days gone-by add to sweet nostalgia, and family fun activities enable the little ones to enjoy the outing.  
  2. If you have not made it out to Middletown for the fourth Saturday in September over the last 30-years, it is time to do so!  Heritage Festival is our landmark festival, much like a homecoming celebration from days gone by, with a parade, lots and lots of vendors, games, activities, several bands throughout the day, and all of your favorite fair foods gathered together to celebrate our history.  And Middletown has over 250-years of history!  We love our history and we love to celebrate it!  This is the event where you see generations of families together – grandma, grandpa, children, grandkids, cousins, aunts, and uncles hanging out together – because this is just how we roll.  This is pure fun and not to be missed.  
  3. And let’s just go ahead and jump to October where we host the most creative scarecrow contest you will ever find, all lined up and down Main Street.  These Scarecrows are just too darn cute to miss, as each year, these hand-crafted scarecrows can be classic, right-on trend, clever, delightful, and super creative.  The Scarecrow’s March on Main starts mid- October and they march away after Halloween.   

If you are looking to make the most of the fall season, we welcome you to Main Street Middletown!