An overnight in Old Town Winchester, Virginia

On a recent trip south, we spent an overnight at Old Town Winchester, Virginia.  This was not a chance stop, I had seen Old Town and purposely booked the stop here.  

George Washington Hotel

Old Town is rich in history.  Right in the heart of Old Town Winchester, is the George Washington Hotel, A Wyndham Grand hotel, where we stayed for the night. The hotel was built in 1924 and is named after George Washington who from 1748 until 1758, spent more nights in Winchester than any other place besides his home.

Walking into the hotel, the roaring twenties come to mind and you feel as if you are a part of history.  The distinctive Tennessee pink marble floor in the lobby is the same floor on which the ordinary people and the famous visitors have walked since the hotel opened in 1924: Jack Dempsey, James Cagney, Ed McMahon, and Lucille Ball.  You will see a signed poster showing Bob Hope in the parking lot entryway.   

The original front desk is beautiful and still has all of the ambiance of a bygone era.   

The old safe proudly stands lodged into its cubby.   

Don’t be alarmed though, this hotel has all the modern amenities after undergoing a $30 million dollar renovation in 2008.  

The old mail slots on each floor drop the mail to the post box on the main floor.

Old Town Winchester

Old Town Winchester is located within the heart of a 45-block National Register Historic District. Within the quaint Loudoun Street pedestrian walking mall, Old Town is sure to have just what you are looking for — an eclectic mix of antiques, fine furnishings, artwork, historic buildings and restaurants, many with outdoor seating.  

Rich in History

For history buffs, Old Town will delight you with its rich Civil War history.  Treat yourself to a ghost tour, the Old Courthouse Civil War Museum,  or see the headquarters of General “Stonewall” Jackson who spent significant time in Winchester during the Civil War.   The house is opened for tours for a minimal fee.  Step further back in time and visit the headquarters of the father of our country, George Washington.  George Washington’s office, where he worked when he was just 16 years old as a surveyor, is a must-see for history buffs. This building has been added onto but still has the original office George used  long before his time as our first president.

Farmers and Merchants National Bank
Shendoah Valley Civil War Museum
Statue of Stonewall Jackson
Old stone house on Loudoun Street
One of the many restaurants on Loudoun Street
Children playing in the water

If you ever get the opportunity to spend some time in Old Town Winchester in Virginia, I highly recommend taking the time to stop and enjoy!


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