The History of Our Bed & Breakfast

The story of the property, where our Chestertown, MD bed and breakfast was later built, begins in 1659 when Josiah Fendall (1628-87), fourth Colonial governor received the land as a gift from Cecil Calvert, Second Lord Baltimore. The name is believed to refer to a large oak tree that marked one of the corners of the property.

Now offering luxury B&B lodging on the Chesapeake Bay, the 12,000-square-foot manor originally was built in 1938 as a private residence for Russell D’Oench. Born out of the bricks from the ballast of W.R. Grace sailing ships, Great Oak Manor was styled after an 18th century English country retreat.

The Georgian-style house has 12 unique rooms, each decorated in a period theme, dressed with Williamsburg paint colors, replica antiques, and private baths.

Front view of our Chestertown B&B

A Tale of the Manor

Great Oak Manor’s rich history dates back to the first recorded land grant when Lord Baltimore gifted the land to Josiah Rendall and Marmaduke Tylden in the 1600’s. The current Manor House was built in 1938 as a private residence for an heir to the W.R. Grace shipping fortune, Russell D’Oench, and his family. Two years into the building of Great Oak, the architect, Douglas Braik, was awarded the Excellence in Maryland Architectural Award for creating the house’s 1700 Georgian detail.

In 1942, the family moved to Washington when D’Oench joined the OSS to serve during the war. Although the move was not considered permanent, they never returned to Great Oak and in 1946 Great Oak Manor (along with the surrounding 1200 acre farm) was sold to a wealthy Ohio manufacturing executive, Frank Russell, owner and Chief Executive of Rusco Storm Windows, Inc.

Frank Russell had a vision to develop a private and incredibly exclusive place on the Upper Eastern Shore, which ultimately evolved into the creation of the county’s finest sportsmen’s club, Great Oak Farm & Lodge. The Manor House was originally the Russell’s private residence, featuring 26 rooms, 9 fireplaces, and 8 baths in over 12,000 square feet of living space. This afforded the Russell family ample space to entertain their prestigious guests. Notable guests included: Arthur Godfrey, Guy Lombardo, Robert Mitchem, Ernest Hemmingway, and Jack Kennedy.

Great Oak Farm & Lodge prospered by the start of the 70’s. Russell invested in recreational offerings including: an 18-hole golf course, 4 star restaurant and lounge, horses, duck and goose blinds for hunting, overnight lodging, a fleet of water crafts including “Rusco”, the 107 ft mother yacht, and a private airport. After a hard day of sporting activities, the gaming room on the Manor’s 3rd floor, now the Russell Suite, served as a gathering place for a friendly game of cards or billiards. Rumor has it that entry in one of those friendly games could go as high as $10,000. After several unsuccessful attempts by the local sheriff to catch guests in these high stakes games, police finally succeeded, forcing Russell to spend 30 days in jail. Undaunted by this moment of adversity, he instructed his staff to prepare his meals as usual, and deliver them to the jail along with place settings and sterling flatware.

Overtime, clientele for the exclusive club began to dwindle and the lodge fell upon hard times, causing Russell to consider selling off Great Oak Farm & Lodge as parcels. In the process, he even instructed his grounds men to cut down many of the property’s mature Black Walnut trees to raise working capital. A good-sized tree could easily bring in 5K, and Russell was looking for any creative means to keep his dream alive. In his quest for quick cash, he failed to inform his workers where the Great Oak property ended and where trespassing began. Neighbors watched in disbelief as their beautiful trees became targets for the saw mills.

The glory days of the Great Oak Farm & Lodge quickly became a thing of the past and nothing more than a burden to Frank Russell, so he auctioned the property off in the early 80’s. The estate was then sold off piecemeal by the Mallon family and subdivided; even as die-hard golfers were at play, 9 of the 18 holes were plowed for more lucrative cash crops, as corn was fast becoming the most profitable industry on the Eastern Shore.

In 1983, a wealthy Philadelphia couple purchased Great Oak Manor and 12 acres of surrounding land. A year later, Great Oak Manor opened for business as Great Oak Manor Bed and Breakfast under a partnered ownership, which went on to acquire six additional B&Bs in the surrounding area. Just as Frank Russell’s Great Oak catered to a high class clientele, so too did the new bed and breakfast operation. Now open to the public, the Manor flourished once again. Eventually though, the partnership outlived its usefulness to investors, and in the early 1990’s, Great Oak Manor was listed for sale with only minimal funds allotted for upkeep.

In 1992, California couple, Don and Diane Cantor, discovered Great Oak Manor while embarking on an extended cruise up the Intracoastal Waterway from Florida to the Chesapeake Bay. Having labored for 30 years in the corporate world, Don realized owning a bed and breakfast would be a fulfilling business alternative. Their strategy for success was simple: bring it back to its former glory through good old-fashioned, hands-on management.

After 9 years, the Cantors officially decided to make more time for friends and family, so they tasked themselves with finding new owners who would care for the Manor with similar, nurturing hands. Their searching ended with Cassandra and John Fedas. In 2000, they took the reins of the Great Oak Manor, adding the conservatory and carriage house. After a decade, they moved to Massachusetts to be closer to family.

In October of 2011, entrepreneur Bernd Duerrmeier could not resist the opportunity to own the property. The German native was no stranger to Maryland’s Eastern Shore. In 1979 he purchased a farm in Queen Anne’s County, where he worked for several years. Unable to remain in one place for too long, he began other projects around the world. However, after returning illness and longing for warmer temperatures, Duerrmeier listed the property once more and left for Mexico.

Business partners since 1989, Buddy Reed and Mike Kuhn purchased Great Oak Manor in February 2015. Reed’s father is an alumnus of Washington College and Reed has been a regular visitor to the Chestertown area, ultimately purchasing a home near Great Oak a decade ago. Both Reed and Kuhn share a construction background and the desire to restore the property to its past prestige. In fact, the first time Reed ever stepped foot on the property, he knew it was something he wanted to own and to be a part of re-establishing its magnificence. In combination with Reed’s resort and hospitality experience, they are maintaining the property as a B&B and positioning it as a premiere destination for weddings, corporate retreats, and group rentals. The pair renovated the under-utilized pool and spa area into an elegant reception area within the conservatory.

Buddy, Mike, and their team have taken great strides to ensure that the Manor feels like home to every guest that discovers the splendor that is Great Oak Manor and hopes to continue a long tradition of welcoming guests to explore, relax, and enjoy the best of the Eastern Shore lifestyle.

Visit Our Eastern Shore Bed & Breakfast

Great Oak Manor offers guests vacation and getaway lodging on the Eastern Shore of Maryland on the outskirts of historic Chestertown. Situated on 12 peaceful acres with a commanding view of the Chesapeake Bay, we are 1 ½ hour’s drive time from Washington, DC, Baltimore, MD and Philadelphia, PA.

GPS Coordinates: Latitude: 39.268718 Longitude: -76.202557


  • Once over the Bay Bridge, stay on Rte 50 to 50/301 split.
  • Take Rte 301 N. to Rte 213 intersection (about 6 mi. past the 50/301 split).
  • Take 213 N. and proceed through Centreville to Chestertown.
  • Once over the Chester River Bridge, turn left at the first traffic light. This is Cross Street. At the next traffic light turn right onto High Street.
  • Follow High Street for 1.1 miles, through the traffic circle, then turn right onto Route 514. 514 turns left in about 3.8 miles
  • Continue on 514 to the stop sign intersecting with Rte 298
  • Cross 298 and proceed 1.8 miles and then turn left onto Great Oak Landing Road.
  • Drive past the farm silos and through the 1st set of red brick pillars.
  • Continue straight past the golf course on your left.
  • Continue straight past the second set of red brick pillars (with the Great Oak Manor sign on your right) to the large red brick manor house.

**Driving time from the Washington DC mall area is about 2 hours and about 1.5 hours from the Baltimore Airport (BWI).

  • Take I95 south to Elkton, MD exits 109 (first exit after the toll booth).
  • Follow Rte 279 thru Elkton to Rte 213 south.
  • Take 213 south past Chesapeake city, Georgetown, and Galena (note 213 turns right at the light in Galena).
  • 7 miles after the right turn on Rte 213 in Galena. you should turn right onto 298 and stay on 298 (it forks left 2.5 miles from the 213 turnoff, and can be tricky at night!)
  • Follow Rte 298 for 11.1 miles from the Rte 213 turnoff then turn right onto Handy
  • Point Road in the tiny town of Melitota. Handy Point Road is opposite Rt.514 to Chestertown
  • Proceed 1.8 miles and then turn left onto Great Oak Landing Road.
  • Drive past the farm silos and through the 1st set of red brick pillars.
  • Continue straight past the golf course on your left.
  • Continue straight past the second set of red brick pillars (with the Great Oak Manor sign on your right) to the large red brick manor house.

**Driving time from Philadelphia is about 1 hour, and 45 minutes, 4.5 hours from NY, and 1 hour from Wilmington, Delaware.

View of Great Oak Manor from above

Tesla Charging Stations

We have two charging stations for electric vehicles that are complimentary use for our guests.