Buckle Up: The Epic Road Trips You Need to Take Before Winter
Even though it technically no longer exists, Route 66 is still a hot item in Yahoo searches. (Photo: Thinkstock)
“The interest in Route 66 increases every year,” Bob Boze Bell says. He’s an expert on historic roads and the author of The 66 Kid. It’s an account of the road he grew up on, during a time when sleepy Kingman, Ariz., was a stop for anyone crossing the country. Bell’s father owned a gas station then, and it’s one of hundreds of places discussed in his book.
“Now as we travel in safety and comfort and — let’s face it — boredom,” he says, “I think we all long for those more exciting days.”
While Route 66 might be the most famous (and, according to Yahoo searches, the road trip our users seek out the most), it isn’t the only highway worth cruising in America. Fill ‘er up, buckle up, and prepare to stop for everything from apple pie to Pigmy goats.
1. Route 66 — Illinois to California
The Hackberry General Store in Arizona along Route 66.
Historic Route 66 offers Americana so prolific, you’d need a month to cover it all. While it technically no longer exists, you can still trace its path. It stretches nearly 2,000 miles, starting in Chicago and ending at the California coast. Driving the entire thing is a bucket list item to be sure, so we asked Bell for his favorite section of the drive.
“Start in Santa Rosa, N.M.,” Bell said, “and then go west into Arizona. That route moves you through the high country, into the Mojave Desert. If you are looking for excitement, it’s one of the most dangerous landscapes on the planet.” (Bring a cooler and provisions — you’ll have long stretches with no options). He continued, “At San Bernardino, you drop into California, and from there the feeling is all Disneyland and Marilyn Monroe. It’s just such an epic journey.”
Where to eat: Delgadillo’s Snow Cap Drive-In in Seligman, Ariz. Built in 1953 from mostly scrap lumber, today it’s decked out in wonderfully stereotypical roadside kitsch. Inside, you’ll find greasy cheeseburgers and walls bearing hundreds of business cards of those who came before you.
Where to stay: The Blue Swallow Motel in Tucumcari. This 1939 motel has been lovingly restored by Kevin and Nancy Mueller, who kept all the funky charm reminiscent of bygone car travel — including the attached garages.
Related: Making Friends on the Loneliest Road in America
2. The Overseas Highway — Florida Keys
The Seven Mile Bridge along the Overseas Highway.
The Keys offer so much — long before you arrive in Key West. There are state parks full of wildlife, quirky restaurants, coastal houses to ogle, and beautiful, boat-filled marinas. The 125-mile trip begins in Florida City and goes over 42 bridges. A portion of the old Seven Mile Bridge in the midway town of Marathon has been open to pedestrian traffic since 1982, and it’s a fantastic photo op. In the lower keys, the old Bahia Honda Bridge stands as a dramatic reminder of the historic Florida Keys Over-Sea Railroad, and you can spend hours soaking up rays at the 524-acre Bahia Honda State Park — a place consistently ranked as one of the best beaches in America.
Eat at: The Hungry Tarpon. Located at Robbie’s Marina, this Islamorada landmark has been operating for 18 years on Lower Matecumbe Key. It’s a great spot for younger kids who’ll enjoy feeding the giant tarpon off the dock. The marina also offers everything from fishing charters to snorkel trips, kayak rentals, and shops.
3. Million Dollar Highway — New Mexico & Colorado
Telluride, off the Million Dollar Highway. (Photo: Jenny Adams)
Officially, the Million Dollar Highway is only 20 miles long. It connects the Colorado mining towns of Silverton and Ouray, along U.S. Highway 50. The drive can be quite hair-raising in sections, as it winds through the Uncompahgre Gorge to the summit of Red Mountain Pass.
Author of the Roadtrip USA series, Jamie Jensen’s familiar with the region. Like many others, Jensen is enamored with the surrounding mountain towns that most people lump in with this drive, even if the towns aren’t officially on the road.
“The only stops along the official Million Dollar Highway are a few pullouts and vista points,” Jensen says. “The ‘high point’ at Red Mountain Pass is 11,018 feet above sea level — one of the highest points on the U.S. highway system.”
Pull off for: Historic Ouray, Colo., is a canyon town with Victorian architecture, abundant hot springs, and hotels ranging from luxe to affordable. Definitely visit Telluride, as well, which has become a posh mountain resort renowned for skiing in the winter and music, art, and film festivals all year long.
4. Great River Road — 10 States From Minnesota to Louisiana
Stop by the Main Street of Galena, Illinois. (Courtesy Galena Jo Daviess Country CVB)
You can travel the Mighty Mississippi by car. The Great River Road touches all 10 states along its border. If you do it fast (don’t do it fast), this trip is roughly 36 hours and 3,000 miles. Thousands of stops await you, but we like the Illinois portion in the fall. Start in the town of Galena, which has a great Main Street filled with 1800s architecture and charming shops. Nauvoo is farther down the route, and it’s an important Mormon town. You can hike to the top of Monks Mound at the Cahokia Mounds State Historic Site, before finishing up in Alton and some great Lewis & Clark sites.
Pull off for: Baxter’s Vineyards in Nauvoo. It’s the state’s oldest winery and a gorgeous place to take a break.
5. The Pacific Coast Highway — California
Admiring the Pacific Coast Highway from the car. (Photo: DiscoverAmerica.com)
There are varying opinions on where the Pacific Coast Highway starts and ends. Officially, California Highway 1 starts in Mendocino County in Northern California and ends in Orange County in Southern California. In between, you’ll hit the jaw-dropping scenery in Big Sur, the coastal vibe of Malibu, and the luxury golf resorts of Pebble Beach. You can pick your pleasure in terms of accommodations along this road, from log cabins with no Wi-Fi to some of America’s elite hotels.
Pull off for: Most of the 20 historical missions in California are along the coast, so you can easily work them into your drive. The architecture alone is enough to make any history nerd swoon.
Where to stay: The Madonna Inn, one of the route’s most famous and quirky hotels. No two rooms are alike here, and all feature hilarious themes.
Related: A Future Road Trip Might be in a Solar-Powered Car
6. Columbia River Highway Scenic Byway — Oregon
The Columbia River Gorge. (Photo: Christian Heeb)
This incredible road spans the extremes of Oregon’s landscape. You start along the mossy banks of the Sandy River, in the town of Troutdale, where the road eventually climbs through orchards and blueberry fields in the communities of Springdale and Corbett. Just as you put them behind you, you’ll next get glimpses of snow-capped Mount Hood.
The Columbia River Gorge is the showstopper of the road trip, spanning 80 miles in length and up to 4,000 feet in depth and cutting the only sea-level route through the Cascade Range. The historic Columbia River Highway gives the best perspectives of the gorge, including sweeping panoramas from 900 feet above the river at one point.
Pull off for: Multnomah Falls. At a mind-blowing 620 feet, only three waterfalls in the nation are taller. A trail from Multnomah Falls Lodge (built in 1925 and listed in the National Register of Historic Places) takes you to the lower cascade, then zigzags you to the top.
What kids love: An afternoon along the Hood River County Fruit Loop. In the fall, the orchards of the Hood River Valley burst with fruit when tree boughs grow heavy with heirloom varieties of apples and pears. The Draper Girls Country Farm has resident Pigmy goats and other cute animals.
An example of the incredible fall foliage here. (Courtesy: Lost Maples State Natural Area)
Whether you do this drive in three hours or three days, we highly recommend taking the trip in the fall. The Lost Maples State Natural Area has hundreds of thousands of Uvalde bigtooth maple trees. When they change in the fall months (peaking between late October and early November), it’s one of the most spectacular foliage displays in the world.
This place can get packed with hikers and bird-watchers (dozens of rare species can be spotted here), so we recommend making this feature of the drive a midweek stop in the fall. Backroads Texas is a great site for the drive’s particulars, including suggestions for lakeside and ranch accommodations.
Where to eat: The Laurel Tree in the town of Utopia. Open only on weekends, it’s worth planning your trip around it. Owner and chef Laurel Waters holds a pastry and wine degree from Le Cordon Bleu in Paris. Her European-style cuisine focuses on seasonal and local foods.
Skyline Drive (Photo: Virginia Aerial Photography)
There are four separate entrances, but most people start at Front Royal in the northwest corner of the state. Entirely within the Shenandoah National Park, the road crests the Blue Ridge Mountains. At 105 miles, it finishes (or starts, if you prefer) in the region of Rockfish Gap near Charlottesville. Unlike some other trips that offer city life within the drive, this one’s a real chance to stay wrapped up in Mother Nature.
Where to stay: Skyland Resort. One of the big lodges, it’s also located at the highest point along the drive, looking west over the valley.
What to eat: Skyland’s Mile High Blackberry Ice Cream Pie. It’s a TripAdvisor darling and apparently big enough to split between two people.
What kids love: The Byrd Visitor Center. But it’s a great stop for anyone doing the drive. Interactive exhibits and movies explain the park’s creation and history, covering geological facts, historical spots, and the various wildlife viewing opportunities.
Related: 15 Apps for the Best Road Trip of Your Life
8. The Blue Ridge Parkway — Virginia & North Carolina
Blue Ridge Parkway (Photo: William A. Bake, Blue Ridge Parkway Association)
Established in 1935, this drive is famous for good reason. Taking over near the end of the Skyline Drive, the two-lane road sends you nearly 500 miles through wilderness, as well as quaint mountain towns like Asheville, N.C. Hop on at the northern entrance near Waynesboro, Va., or the southern entrance near Cherokee, N.C. The speed limit is 45 mph or lower in some regions, so plan for at least two full days of travel if you want to complete the drive — more if you want to enjoy it. For travelers who want to stay officially on the parkway, there are multiple National Park Service campgrounds and two parkway lodges.
Where to stay: Peaks of Otter Lodge near Bedford, Va., open since the 1960s. The lodge has 63 rooms and great dining options, all overlooking Abbott Lake. Don’t worry — you won’t be bothered in your quaint accommodations here by those pesky, modern-day hassles like Wi-Fi and phones.
Take note: There is no fee to enter the parkway, and the road is open year-round, weather permitting. However, road closures are frequent from late November through April, when precipitation often makes the road unsafe. A real-time road closure map is updated daily at www.nps.gov/blri so visitors can check road conditions before heading out.
10. Black River Scenic Byway — Michigan
(Photo: xray10/Flickr)
The Black River Scenic Byway is an officially designated National Forest scenic byway. What does that mean? It’s gorgeous and full of waterfalls, boats rocking lazily in charming harbors, trailheads, and the world’s tallest ski jump, naturally. You begin in Bessemer, Mich., on Highway 2 and travel all the way to Lake Superior.
Pull off for: There are two don’t-miss spots. The first is the waterfalls of the Ottawa National Forest. These are located in the last three miles of the drive and are very clearly marked. You should also make time for a picnic at the Black River Harbor. Here you’ll find a concession stand, a suspension bridge, a swimming beach, forest hiking trails, and a campground.
Quirkiest spot: The Copper Peak Flying Hill. It’s the tallest ski jump in the Western Hemisphere. In fact, it’s so high, the sport is technically called ski flying, not jumping.
WATCH: Route 66 Gets Musical to Stop Speeders
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