Cool Summer Car Events

When: July 14-17
Where: Road America, Elkhart Lake, Wis.

Another event at Road America, another excuse to see Wisconsin's lovely rolling countryside. The Kohler International Challenge is the country's most laid-back vintage race extravaganza, a mind-melting gathering of Can-Am cars, old Formula One iron and enough American muscle to make Detroit jealous. No other track in America is big enough to let these old dogs stretch their legs, either — how does 180-plus-mph sound? Don't forget to sample the concession-stand pie.

View Pictures:  High Performance

When: July 15-16
Where: Newry, Maine; Mexico, Maine; Errol, N.H.

New England is pretty in the summer. Its forests are filled with green leaves and rushing rivers; its shores are teeming with wildlife; and every weekend you can find someone having a serious clambake. Once a year, professional road rallying — production-based racing cars on closed roads going as fast as their drivers can make them — comes to the area, making it even prettier. The New England Forest Rally is part summer festival and part joyous speed party. Its drivers are accessible, its cars are relatable and the fun is nonstop. Admission is free, so all it takes to attend is some sunscreen.

Bing: Rally Racing

When: July 16
Where: Keeneland Race Course, Lexington, Ky.

Alfa Romeo left this country a decade and a half ago, but enthusiasm for the Italian marque is still going strong. Now that Alfas have mostly retired from daily-driver use, the best place to see them is at the Alfa Romeo Owner's Club's national concours. This year's iteration takes place in Lexington, Ky., at the Keeneland horse-racing track. Alfas are gorgeous and sound amazing, and Kentucky horse country makes for a relaxing Southern vacation.

View Slideshow:  2011's Best Pace Cars

When: July 22-24
Where: Schenley Park, Pittsburgh

Pittsburgh isn't known for motorsports. But the Pittsburgh Vintage Grand Prix is a special event. Every summer, the roads inside one of the city's public parks are closed off, and vintage racing cars take to the pavement. They race around the park for a weekend, rocketing picnic-blanket spectators back to the days when speed was simple and hay bales were all the crowd control you needed.

Watch Video:  Pittsburg Vintage Grand Prix

When: Aug. 5-7
Where: Carlisle Fairgrounds, Carlisle, Pa.

Who doesn't love trucks? Judging by the annual attendance at the Carlisle Truck Nationals, nobody, that's who. This massive gathering of ladder-frame lovelies features everything from a swap meet to a showing of slick 18-wheelers. Lifted trucks, lowered trucks, monster trucks, 4x4s, minitrucks, a burnout competition — the list goes on. There's even a midway for the family. This is the kind of single-focus mania we can't help but applaud.

View Slideshow:  Real Off-Road Warriors

When: Aug. 18-21
Where: Mazda Raceway Laguna Seca/Pebble Beach Golf Links, Monterey, Calif.

The Monterey Weekend, as it's come to be known, is the West Coast's single most impressive car gathering. It encompasses the famed Pebble Beach Concours d'Elegance, historic racing at Laguna Seca, countless wine-and-cheese shows and more street-driven Ferraris than you can shake a Weber carburetor at. The rich and famous flock here for events like the exclusive Monterey Jet Center party, but the weekend is equally accessible for ordinary folk. No matter your income, it's an all-encompassing and wonderful experience.

View Pictures:  Vintage Ferraris

When: Aug. 20
Where: Woodward Avenue, Detroit

Detroit knows cruising, and the Woodward Dream Cruise is the biggest one in the world. This is essentially the world's largest car parade, a 40,000-vehicle event that stretches the length of the Motor City's famed Woodward Avenue. Muscle cars, classics and tamed racers jam the pavement, and more than 1 million people come to watch or participate. You can drive your own car in the cruise — it's free — or simply set up camp on the sidewalk and watch.

Read:  Rollin' It Retro

When: Oct. 14-16
Where: Mazda Raceway Laguna Seca, Monterey, Calif.

This one's a bit late for summer, but it's so spectacular — and so rare — that we had to include it. Porsche's triennial Rennsport Reunion is the world's coolest Porsche-only gathering, a combination vintage race, Oktoberfest and rolling museum. This year's event takes place at Laguna Seca; famous drivers and legendary cars are guaranteed to attend. If you want to see Germany's greatest sports-car company pull out all the stops at triple-digit speeds, this is the place.

Bing Images: Porsches

Sam Smith is a journalist, a Southerner, and a reformed Alfa Romeo mechanic who spends most of his time mooning over leaky old motorcycles and small-batch bourbon. A multiple International Automotive Media award-winner, he has covered cars for Automobile Magazine, Car and Driver, and Esquire, among other publications. He once drove 4000 miles in a weekend for a hamburger and has only been threatened by the German police twice.

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