The Best Small Wedding Venues in Chestertown, MD

The Best Small Wedding Venues in Chestertown, MD

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2 Wedding Venues in Chestertown, MD

Farms, barns, ranches
Up to 50 guests
Available on September 13, 2026
Quick responder
Drumore Mill 

5.0

  • Up to 125 guests
  • Select services
  • Outdoor
  • Starts at $4,700

Drumore Mill is a different world. It is nestled in a corner of the most rustic township in Amish Lancaster County, Pennsylvania. The mill was built in 1752 as a sawmill and a grist mill. It sits in a hollow with 30 acres of tall cliffs and old trees to provide privacy, warmth, and natural beauties. There is a pristine creek that meanders through the property. The Fishing Creek supports native trout and other rare small fishes. The waterfall is adjacent to the buildings. There is a hiking trail within the property. There is wetland and much more. The combination of rustic setting, natural beauties, and historical features makes Drumore Mill amazingly beautiful. One has to see it to believe it.

Why you'll love this venue

  • Venue is completely outdoors
  • Provides setup and cleanup
  • Has a glamorous vibe

Venue considerations

  • Does not allow pets
  • Not for you if you're looking for a sleek and contemporary space
  • Additional event staff required
Awarded Best of Zola
Drumore Mill was an absolutely stunning venue to use for our special day (really weekend). We loved the ease of booking the venue, touring with Thuy, and the promptness and flexibility they offer. An added bonus is the available on site lodging for rental, which we made great use of for our close friends, family, and wedding party to stay in the night before and night of the wedding. We enjoyed the Great Room in the Grist Mill for our rehearsal dinner. Our guests loved how spacious Drumore Mill was, and we appreciated all the attention to detail such as included (but still optional) decor and greenery, and the setup of chairs and other items for the ceremony space. Being able to bring in all of our own vendors at no additional cost was fantastic. The value for renting the property from Thursday to Saturday morning was unmatched and completely worth it. We would recommend Drumore Mill to anyone, and we look forward to booking the property in the future for non-wedding related stays with friends and family.
Maureen B., 10 months ago
Stepne Manor 
Chestertown, MD
  • Up to 250 guests
  • Raw space
  • Outdoor

Brittland Estates embraces a collection of heritage properties located in the historic Chestertown area of Maryland's Eastern Shore. Its distinctive properties are rich with history, expansive settings from fields to rivers, and a rural sophistication. Each property is an ideal venue for weddings, small retreats and meetings, reunions, and get-a-ways. Stepne Manor is a marvelous property. Boasting a front porch that looks out onto the expansive lawns, there is a cultivated sophistication to the building’s exterior. After you have been joined in matrimony at your outdoor ceremony, make your way indoors to delight at the interiors. Here, there is a great deal to appreciate. Stepne Manor’s dining room provides space for you and your guests to sit and eat, while the kitchen affords any hired culinary staff with an ideal preparation base. The great room, den, and sun porch provide ample room for everyone to kick back, relax, and enjoy the festivities.

Why you'll love this venue

  • Wheelchair accessible
  • Caters to out-of-town guests
  • Raw space for complete customization

Venue considerations

  • Venue feels large for events with small guest lists
  • No on-site bridal suite
  • Does not allow pets

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