About The Races

FAQ, Schedule, and Directions

To contact us, please e-mail crystalsecretary@comcast.net.
(click to expand)

What are the Howard County Cup Races?

A Howard County family tradition for close to 70 years, the race meet showcases one of Maryland's most historic sports, horse racing over the open countryside, jumping over natural fences. Spectators enjoy an outdoor party, vying for "Best Tailgate Awards" while cheering on the horses and riders.

Although horse sports date back to Maryland's Colonial days, modern day equestrian activities, from lesson stables to horse shows, have become Maryland's largest agricultural industry, with an annual economic impact of over $1.5 billion.

When and where are the Howard County Cup Races?

The first Saturday in May - See schedule below.
Pleasant Prospect Farm
4389 Jennings Chapel Road
Brookeville, MD (Just off of Route 97)

The race meet is in the cradle of Howard's "rural west," in the picturesque valley of Jennings Chapel Road, easily accessible from all points, including Mt. Airy, I-70, Ellicott City, Columbia, Clarksville, Olney and Damascus.

See directions below.

Who goes to the Howard County Cup Races?

The Howard County-Iron Bridge Race Meet is the only activity to bring together "old Howard County" with "new Howard County." Howard County is one of the three wealthiest counties in the entire U.S., not to mention one of the fastest growing. Howard's new residents have embraced the opportunities offered by "the rural west," immersing themselves in the county's horse sports - and the races are a popular sports outing for all Howard Countians, not just the ones involved with horses. Howard Countians enjoy the opportunity to welcome spring by being outdoors, to enjoy the tradition, to enjoy the sporting entertainment, and the opportunities to meet new friends and neighbors, or to catch up with old acquaintances.

What does "Heads up!" mean?

  • Please do not allow children (or adults) to play on the racecourse at any time.
  • At all times, horses have the right of way.
  • If you hear “HEADS UP,” that means to clear the way for the horses.

Tailgating Guidelines

  • Please plan to take-out anything you bring-in, including all trash and garbage.
  • There is no electrical or water hookup for tailgates.
  • Portable tents and small grills are permissible.

What do I wear?

Gentlemen traditionally wear button-down shirts with khakis, sometimes with ties and/or blazers or sport coats (depending upon the weather and the type of tailgate party), and sometimes with a hat or cap (appropriate for the weather).

Ladies traditionally tend to be sensible on the lower half, but often dress it up a bit on the top half! Ladies who choose heels generally later regret the choice. Some ladies may choose to wear “Derby Hats!” Have fun with it!

May I bring my dog?

We prefer not, as does our insurance company. Those that do bring their dogs are required to keep them leashed. There will be horses everywhere, foxhounds on parade, and a variety of breeds performing with “Disc Dogs.”

Do I need 4 wheel drive?

Only if it rains.

Can I host my Kentucky Derby party at the Howard County Cup Races?

Absolutely! See our tickets page to purchase tickets.

Where will we be able to watch the Kentucky Derby?

After the last live horse race, the corporate tent will open for all spectators, free of charge (there will be a cash bar inside); there will be plenty of viewing screens inside and around the tent.

Is there a rain date?

Yes, the Sunday immediately following. If inclement weather forces the cancellation of both days, the races will not be rescheduled.


12:30 pm Gates Open for spectators to begin setting up tailgates.
2:00 pm Tailate Contest Judging begins
2:30 pm Opening Ceremonies
2:45 pm Riders to the paddock, please.
3:00 pm Post time, first race
6:46 pm Kentucky Derby airs
7:00 pm Event Concludes

Directions to Pleasant Prospect Farm

4389 Jennings Chapel Road
Brookeville, MD 20833

From Baltimore/Washington

Take I-695 to I-70 heading West
Take Route 97 South
Make a right on Jennings Chapel Road
Pleasant Prospect Farm will be on your right

From Points South/D.C. Beltway/495

Take Route 97 North
Cross river into Howard County
Make a Left on Jennings Chapel Road
Pleasant Prospect Farm will be on your right

From Annapolis

Take I-97 North
Take Route 32 West
Make a left on Burntwoods Road
Go left/South on Route 97
Right on Jennings Chapel Rd
Pleasant Prospect Farm will be on your right

Interactive Map


Presented By

The 2014 Howard County Cup Races are presented by

M.T. LaneySEH