4 Classic Road Trips for a Nostalgic Summer Trip


There’s nothing quite like the open road, whether you’re traveling by motorcycle, cozy coupe, converted van, or a full-sized RV. Unlike a lot of other vacations, road trips offer a great deal of spontaneity, and depending upon where you live, it can be easy to set out for adventure with minor planning to satisfy your wanderlust.

If you’re ready for a last-minute summer trip or daydreaming about an adventure for a later date, the first step is talking to Westwood to be sure you’ve got the right auto insurance. Once you have the right coverage, you’ll be ready to check out one of these four classic road trips and enjoy the nostalgic, go-at-your-own-pace relaxation that comes with a long car cruise.

Route 66

The often-lauded Route 66 is perhaps the quintessential road trip. Stretching all the way from Chicago, IL, to Santa Monica, CA, this trip allows you to cross most of the Midwest, see the Great Plans, and even enter the Southwest.

This route is a significant time commitment, as it crosses most of the country and will also take some careful planning to complete. You can no longer drive Route 66 uninterrupted from Chicago to Los Angeles. In the 1960s, sections of Route 66 were replaced by other roads. You can still travel on remnants of the original route, such as Routes 366, 266, and 66 in Missouri, but in some areas, you’ll have to travel along the roads that replaced it.

The trip is still worth the drive as, in the late 1980s, a revival of Route 66 took hold. Preservation groups have saved, restored, and even landmarked old motels and neon signs along the road in some states. The National Park Service developed a Route 66 travel itinerary, Discover Our Shared Heritage which lists over 100 historical sites that can be seen from the original route, such as trading posts, drive-in movie theatres, gas stations, motels, and cafes.

Pacific Coast Highway

Perhaps equally famous to Route 66 is the Pacific Coast Highway, the West Coast drive that hugs California’s coast and takes drivers from Los Angeles to San Francisco. Though this trek can be completed in just one day, its scenery is worth stretching the trip with an overnight stay.

Carmel by the Sea is a little town just a short drive from Monterey and offers a great seaside location with charming cafes and an easygoing pace. Half Moon Bay, just forty-five minutes from San Francisco, offers the perks of wine country with less of the hustle and bustle, and of course, you’ll also have easy access to plenty of picturesque beaches. If you’re looking for a livelier stopover, then Santa Cruz might be the place for you, especially with its famous Boardwalk, which was voted the World’s Best Seaside Park.

New Port to New York City

The Pacific Coast Highway gets a lot of love, but the East Coast has some great routes too. One of the most famous treks is the drive between Newport, RI, and New York City, NY. Much like the renowned road trip on the West Coast, this trip can be completed in a single day, but there are plenty of stops worth your time, everything from the Mark Twain House & Museum to the interactive Mystic Aquarium.

Recreation along this drive includes Lake Compounce water and amusement park, surfing at Narragansett Beach, and skydiving excursions at Skydive Danielson. Those who love culture and history buffs can visit places like the Seaport Museum in Mystic, take a guided tour of historic sites of the Connecticut River Valley by traditional riverboat or steam train, or wander the exhibits of the Wadsworth Atheneum Museum of Art. There are also plenty of shops and dining places like Elephant’s Truck Flea Market and Costantino’s Venda Bar & Ristorante.

Blue Ridge Parkway

Called “America’s Favorite Drive” by USA Today, this 470-mile long route stretches from Shenandoah National Park in Virginia to Great Smoky Mountains National Park and ending North Carolina. It’s difficult to rival this road trip when it comes to scenery, as it boasts many breathtaking views.

Among the many recommended stops is Milepost 85.9, Peaks of Otter, where you can even make reservations at Peaks of Otter Lodge. Even if you don’t want to spend the night, the lodge offers a great restaurant where you can dine overlooking the lake. From here, you can hike around Abbott Lake itself or take Sharp Top Trail for an incredible view of the landscape.

Historic towns like Roanoke and Floyd offer old-fashioned stores and restaurants, and the caverns at Natural Bridge allow you to descend nearly 35 stories into the ground. Mabry Mill is a famous spot for photography enthusiasts and history buffs. The area is frequently flanked by wildflowers or autumn leaves and still offers live milling demonstrations of processes used since the early 1900s. If you’re a music enthusiast, you’ll also want to stop by the Blue Ridge Music Center to take in the sound of the fiddle, guitar, and banjo at daily outdoor concerts.

Wherever you go, take Westwood with you

A road trip gives you the freedom to enjoy the journey and not worry so much about the destination. Whether you’re retracing a road trip you took with your parents years ago, venturing out on a well-researched drive you’ve heard about on your favorite travel blog, or are looking to explore a whole new route spontaneously, take us with you.

Westwood can help you be sure you’ve got the right auto insurance to cover all your trips, from crossing the country to running an errand across town. Reach out today or get a quote to find the right policy for you.

Please Note: This article is for general informational and educational purposes only. It does not represent any specific insurance policy and does not modify any provisions, limitations, or exclusions of any current policy.