The Best Historic Estate & Mansion Wedding Venues in Chestertown, MD

The Best Historic Estate & Mansion Wedding Venues in Chestertown, MD

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5 Wedding Venues in Chestertown, MD

Historic estates, mansions
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., a year ago
Quick responder
King Cole Farm 

5.0

  • Up to 300 guests
  • Select services
  • Indoor & outdoor
  • Starts at $3,000
  • Offer

Your premier destination for a picturesque and enchanting wedding venue in Dover, Delaware. Nestled amidst scenic landscapes, our modern farm offers an idyllic setting for couples seeking an unforgettable celebration. As one of the top wedding venues in the Mid-Atlantic region, we pride ourselves on creating magical moments for your special day. Our charming farm, reminiscent of a fairytale, is perfect for those dreaming of a Castle wedding or seeking rustic elegance in barn wedding venues in Delaware. With sprawling fields and breathtaking views, King Cole Farm provides an unparalleled backdrop for your ceremony and reception. Whether you envision a cozy barn wedding or an outdoor celebration surrounded by nature, our versatile event spaces cater to your desires. Located conveniently near Dover, our farm offers a tranquil escape while remaining accessible to the city. Our facilities in Dover, Delaware, provide ample space for your guests to revel in the joyous occasion.

Why you'll love this venue

  • Both indoor and outdoor options
  • Rustic charm with elegance
  • Private area for the wedding party

Venue considerations

  • Not for you if you don't want a rustic vibe
  • No all-inclusive dining options
  • No built-in audiovisual options
From our first meeting with Rachel at King Cole Farm, we knew we were in good hands. Rachel was outstanding throughout the entire process - from our initial visit to the day of the event and even in the days after. She always had a warm smile on her face and took care of anything that came up, no matter how big or small. Rachel put us at ease and made the entire weekend a fabulous experience. The venue itself is absolutely stunning. The beautiful scenery where the ceremony took place, the lovely cocktail hour space, and the grand barn doors that the wedding party walked through - it was all an amazing experience. There was plenty of room for the caterer, bar, desserts, late night snacks, and of course, dancing! On the day of the event, we had the pleasure of working with the intern as well. She was so kind, giving rides to the ceremony and back to the cocktail hour and house for our elderly guests. She also helped us with the cleanup at the end of the night. The entire King Cole Farm staff is truly top-notch. I am still getting phone calls, text messages and social media posts that it was the best wedding they have ever attended! I would highly recommend King Cole Farm to any couple looking for a beautiful, well-run wedding venue. We had such a wonderful experience, and I hope to use them again in the future!
Melinda D., 6 days 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
Brittland Manor/ River Lodge 
Chestertown, MD
  • Up to 400 guests
  • Raw space
  • Outdoor
  • Starts at $45,000

Historic mansion, river vistas and forever fields, the world of Brittland personifies an old world luxury elegance in a rural setting. The hilltop setting commands magnificent views of the Chester River. Brittland Manor gives the discerning couple a series of settings and moods to create their distinctive celebration. This secluded mansion has a garden, pool, wildlife pond, 530 riverside acres, and woodside fields. A waterfront cottage perfectly compliments the 530 acre Brittland Manor estate. It offers a rustic riverside setting for ceremony and/or a rehearsal dinner.

Why you'll love this venue

  • Wheelchair accessible
  • Rustic yet refined style
  • Surrounded by nature

Venue considerations

  • Does not allow pets
  • No venue-provided food services
  • Does not have a dance floor

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