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Road Trip Ideas for May

Across the country, the merry month of May marks the start of summer, and for many people, May also means it’s time to go off to the races. On May 4th over 100,000 lovers of thoroughbred horses (and mint juleps!) made their ways to Louisville for the soggiest and most controversial Kentucky Derby in recent memory, while some 300,000 motorheads will get together at the end of May at the Indy 500 in Indianapolis.

Meanwhile, out west in nonconformist California, a very different pair of races mark the onset of summer and bookend one of the country’s greatest road trips: a leisurely cruise among the wineries and redwood trees of the Northern California coast. Starting in San Francisco, the world’s largest, oldest and craziest footrace, the Bay-to-Breakers, takes place on May 19th, when some 75,000 runners make their way across the city. Top athletes complete the hilly 7.5-mile course in less than 40 minutes, but for spectators most of the fun is in cheering on the rest of the pack, many of whom are dressed in outrageous costumes.

Heading north from the City by the Bay, cross the Golden Gate Bridge and tour the famous wineries of Napa and Sonoma, where numerous country lanes off high-speed US-101 are lined by quaint towns and an abundance of great restaurants. Or if the weather’s fine and you have more time, make your way along coastal Hwy-1, which winds along the rugged coast through the pastoral valleys of Point Reyes and the historic logging town-turned-art colony of Mendocino.

The incredibly scenic coast and valley roads come together further north at the Avenue of the Giants amidst the mighty redwood trees of Humboldt County, where another wacky race shows off the individualistic energy California is famous for. Held each Memorial Day weekend since 1969, the Kinetic Grand Championship is a three-day celebration of people-power, in which teams of contestants pedal, push, and paddle creatively designed mobile sculptures through the towns of Arcata, Eureka and Ferndale, racing along city streets, country roads and across sandy beaches and chilly bays. Unforgettable fun.

Other roads to drive in May:

A Tour de Texas on US-83

Southwest Texas, especially the Hill Country area along US-83 west of San Antonio, is one of the most beautiful corners of the Lone Star State, and May is a lovely time to visit (especially if you can make it to the Kerrville Folk Festival, which takes place over 18 days and nights starting Memorial Day weekend).

A longhorn cow stands in a field of wildflowers in Texas HIll Country.
Photo © Rauluminate/iStock.

In late spring, while the rolling hills are still green from the winter rains, all over the Hill Country region you’ll see bluebonnets, a wild lupin that’s the Texas state flower, in peak bloom along the roadsides, while rivers flow past sleepy Wild West hamlets like Leakey and idyllic Utopia. Besides being heaven for road-trippers, the Hill Country region is also ideal for cyclists and motorcyclists.

And as always, Remember the Alamo! The historic chapel and battle site sits right at the heart of San Antonio, a bustling and very welcoming modern city that make as a great gateway to this ever-enjoyable, multi-cultural corner of the USA.

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