Annual Events

Mt. Sharon gardens 2009 Historic Garden WeekVirginia Festival of the Book
Where: Charlottesville
When: Late March

A week of mostly free literary events open to the public to honor book culture and promote reading and literacy.


Historic Garden Week
Where: Orange County
When: Mid-April.

The Garden Club of Virginia presents historic garden tours all over the state, and Orange County properties are annual participants. Tours present a rich mosaic of some of the country’s finest properties at the peak of Virginia’s springtime color.


Montpelier Wine Festival
Montpelier Wine FestivalWhere:James Madison's Montpelier
When: Last weekend in April or first weekend in May.

The Montpelier Wine Festival showcases distinctive arts and crafts, specialty food vendors, live music, "cooking with wine" classes, children's entertainment and rides, and Virginia wine tastings all day.



Graves Mountain Bluegrass Festival
Where: Nearby in Syria, Virginia, in the Blue Ridge Mountains.
When: Late May/Early June

Bringing the very best of bluegrass talent to Central Virginia.


Castleton Festival
Castleton Festival, Maestro MaazelWhere: Northwest of Culpeper, VA at Castleton Farms.
When: Throughout July

An amazing festival of the arts in a picturesque rural setting, the Castleton Festival is the signature event of The Chateauville Foundation. Enjoy a month-long line-up of opera, symphonic concerts, dance and puppetry! Pre- and post-show concert talks, recitals, informal chamber music concerts and cabaret are also available.


Orange County Fair
Orange Counnty Virginia Fair

Where: Orange County, not far from our bed and breakfast in Orange

When: July

Orange celebrates its role in American history, its agricultural heritage, and the traditional values that created and help sustain a way of life. The Orange County Fair is an old fashioned county fair in the truest sense; no midway carnival, no high pressure selling activities, but plenty of activities, contests, and entertainment aimed at creating a fun atmosphere for everyone! Check out their website for more information about some of the nationally-recognized entertainment that the fair brings to Orange County!



Somerset Steam and Gas Pasture Party

Somerset Steam and Gas Association Pasture PartyWhere: Somerset, VA, only about 3-4 miles from our inn
When: Mid-September.

This is one of our favorite annual events -- it's always great fun and extremely interesting! The Pasture Party displays exhibits of fully-operational antique steam boilers and engines, gas engines, tractors, agricultural equipment, and industrial equipment. A fantastic way to experience how work was done in a bygone era. Includes numerous demonstrations of threshing, baling, sawing and any other displays or demonstrations that are in keeping with the theme of the event. Gorgeous antique and classic cars are also on display, and there's plenty of food, antiques, and local crafts for sale!


Orange Street FestivalOrange, Virginia Street Festival

Where: Main Street in Orange, VA, right in front of our bed and breakfast!
When: The Saturday after Labor Day.

Hundreds of food, arts and crafts vendors display their wares to over 15,000 people.




Fall Fiber Festival and Montpelier Sheepdog Trials
Fiber Festival and Montpelier Sheep Dog TrialsWhere: Near Montpelier, about 2 miles away from the Holladay House Bed and Breakfast
When: First weekend in October.

From animal to fiber to finished craft, this show tells the whole story. Keep busy with exhibitors, guest speakers, workshops and crafts for sale. Sheepdog trials are a must see as well!


Montpelier Hunt Races
Montpelier Hunt RacesWhere: James Madison's Montpelier
 When: First weekend in November.

Started in 1924 by Marion DuPont Scott, the hurdle course features the only live brush jumps in the Commonwealth of Virginia. This equestrian event is a long-standing Virginia tradition, boasting some of the oldest continually-used steeplechase hedge rows in the country. Attendees from all over the country stay at our Virginia bed and Breakfast to see this exciting event, where elaborate tents, tailgating, and traditional hats are the order of the day!


Christmas Parade
Where: Main Street, Orange, Virginia
When: The first full weekend in December.

Enjoy an extensive small town parade featuring antique cars, local bands, volunteer organizations, and Santa in his sleigh!