Annual Events

Mt. Sharon gardens 2009 Historic Garden WeekBBQ Exchange Porkapalooza
Where: Gordonsville
When: mid-February

A most excellent celebration of pork with an all-you-can-eat feast by one of the best chefs in the region! A ticketed event (fastest way to get to the food line) of about $20/person including food, drinks, music and family-friendly activities! A tented event to help protect the food (and you!) from the winter elements.


Virginia 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.


Orange Uncorked Wine Festival
Where: (last year at Montpelier!) 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.


Gnarly Hops and Barley Fest
Where: Downtown Historic Culpeper, in the Spencer Street parking lot
When: Last Saturday in April

This event will feature over 70 different craft beers, live music, exhibitors, and great local food. Only a limited number of advanced tickets will be on sale, so get your tickets online OR at the gate for a little bit more.  Usually held from Noon - 5pm, enjoy Downtown Historic Culpeper afterwards!


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.


Rodeos at Oakland Heights Farm

Where: 6 miles from the inn
When: 2nd Saturday of each month May - September

BLM Bull & Rodeo Company are producers of some of Virginia’s finest Professional Bull Riding events and were voted Producer of the Year in 2009 by SEBRA.  Family-friendly event with music and food!


Fried Chicken Festival

Where: Gordonsville, 10 miles from the inn
When: May

Gordonsville is famous for its fried chicken, which was served to passengers of trains stopping in town during the late 19th and early 20th centuries by local women carrying platters of the delicacy on their heads. Nationally-known at that time, Gordonsville's fried chicken earned the town the nickname of "chicken-leg center of the universe".


Trashy Ribs and Blues Festival
Where: 2 blocks down Main Street from the inn!
When: June, usually Father's Day Weekend Saturday

Think thick, juicy, dripping ribs, coleslaw, beans, rolls and cold, oh-so-cold, beverages. Then, while you’re wiping the sauce from your face and fingers you hear some of that solid, harmonica-based, funky blues from well-known bands and you can’t help tapping your feet and smiling. Get it? A craft brews and ribs festival right here in downtown Orange.


Orange County Fair
Orange Counnty Virginia Fair

Where: Orange County Fairgrounds, 3 miles from the inn

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!




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.


Where: Downtown Historic Culpeper Depot District, 20 minutes from the inn
When: early-September

Celebrate craft beer at Hoptoberfest!  Almost 100 craft brews to try, live music, fantastic food trucks and a great atmosphere!  Tickets in advance or at the gate.


Somerset Steam and Gas Pasture Party

Somerset Steam and Gas Association Pasture PartyWhere: Somerset, VA, about 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!


Pickers Paradise
Where: The Market at Grelen, 6 miles from the inn
When: September

Pickers Paradise is an upcycled flea market.  There is a wonderful selection of local vendors as well as music, farm fresh lunch options & Virginia Beer, Cider & Wine!


Constitution Day at James Madison's Montpelier
Where: James Madison's Montpelier, 3 miles from the inn
When: mid-September

Tour the stunning grounds and home of the Father of the Constitution for free!  A family-friendly day with activities for all ages including hands-on history activities, food, music, and more!



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!


Chili Cook-Off and Brew Festival
Where: Orange County Fairgrounds, about 3 miles from the Holladay House Bed and Breakfast
When: mid-October

Hosted on the lovely Orange County Fairgrounds, sample chili from amateur cooks and professional chefs and cast your vote!  Your admission ticket entitles you to 10 craft beer tastings and a souvenier mug.  Bring a seat and kick back to enjoy live music and a great atmosphere!


Montpelier Hunt RacesMontpelier Hunt Races
Where: James Madison's Montpelier
When: First Saturday 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!


CiderFest at Castle Hill Cider
Where: Castle Hill Cider, 15 miles from the inn
When: mid-November, part of Virginia's Cider Week

The picturesque grounds of Castle Hill Cider hosts the annual celebration of wine cider!  Hosting wine cider producers, fantastic food trucks, live bands and games for the family.  Advance tickets available and regular admission at the gate.


Downtown Holiday Village
Where: Main Street, Orange, Virginia; Market at Grelen and James Madison's Montpelier
When: First weekend in December

Downtown Orange becomes an old-fashioned village filled with holiday music, seasonal vendors and Santa! The event will bring together live holiday music, downtown merchant Open Houses, a Makers Craft Village, food, children’s activities and local church bazaars.

James Madison's Montpelier has a special open house. Montpelier is open to the public for free with festival era-appropriate music and costumed interpreters. Enchanted Extravaganza a great shopping experience filled with upcycled and handmade items for the holidays.  Hosted in a beautiful clear tent, it's the perfect start to the holiday shopping season.  Along with a great selection of vendors, comes holiday music, Santa and fresh fare.

On Sunday afternoon, enjoy an extensive small town parade featuring antique cars, local bands, volunteer organizations, and Santa in his sleigh!