Two months, four reasons to wing it: betting on the jumpers in Virginia; partying with the crew at Head of the Charles; quaffing ales with connoisseurs in London and helping the Vineyard start a delicious new tradition.

International Gold Cup, October 20

Marking its seventieth run with a top purse of $100,000, this all-day spectacle is the cream of the fall steeplechase crop. Many of the world’s top thoroughbreds (and we don’t just mean horses) descend on The Plains, Virginia, for this event, so bring your blue book and pencils. The racing dailies don’t come out until the Monday of race week, and then the touts go to work. Care to wager a quid or two? Look for the chalkboards and ask revelers to point out their bookie.

Private tailgates at rail 4 on Members Hill ($650 with tent) are the best spot — or pony up $35 for a Hill Badge and crash the gated scene. Finish the night at the after-hours party at Robbie Banner’s working horse farm, sipping hard cider by roaring bonfires and disco dancing in a 300-year-old barn.
Fly into Winchester Regional Airport (runway 5,500 feet). vagoldcup.com

Head of the Charles, October 20–21

Take part in America’s classiest kegger as 7,500 athletes and their nubile young fans converge on Boston’s storied waterway. Saturday’s best view is of the “powerhouse stretch” from the Weeks Foot Bridge. For a comfier patch, you’ll want to wake up early to stake out a spot on the grass near Eliot Bridge or else secure an invitation to picnic in style with Bloodies at Radcliff Weld Boathouse.

Coeds and active and out-to-pasture rowing studs contribute to the pretty people–watching post-race by the tents at Reunion Village. Or throw your own regatta party by buying a VIP tent for $5,000 — silver platters, full bar and catering not included. Don’t forget to brush up on your rowing terms (and hit the rowing machine at the gym) if you plan to impersonate a former elite skull man.
Fly into LG Hanscom Field Airport, Concord (runway 7,000 feet). hocr.org

London Bierfest, October 10–12

Munich’s Oktoberfest a little too much for you? Celebrate the sudsy season with the gents and lasses at London’s Old Billingsgate Market. A 10-person tent table ($2,100) comes with unlimited servings of Paulaner beer. Thursday is the favored night, packing in a crowd of lads fraternizing at corporate tables; they stay until after the music ends . . . or until they’re carried out.
Fly into London Biggin Hill Airport (runway 5,912 feet). londonbierfest.com

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