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Planes allow you to travel quickly around the U.S., but if your journey is the destination, take to the roads to explore the country’s dazzling array of landscapes at a slower pace. If you need some road-tripping inspiration, check out our post on Maximizing Points and Miles on Road Trips—and allow new TPG Contributor Spencer Spellman to guide you along some of the best driving routes in America.
Route 66 – California to/from Illinois
Dating back to 1926, Route 66 is one of America’s original highways, and with its well-preserved historic sites and wide-open landscapes, it’s essentially the poster child for the American road trip. In each state it runs through, you’ll find distinctive landmarks like Arizona’s Jack Rabbit Trading Post, a popular pitstop for travelers for more than a half-century. New Mexico’s 400-mile section is lined with Native American monuments and centuries-old ruins like Laguna Pueblo, and in Amarillo, Texas, the famous Cadillac Ranch art installation features rows of graffiti-painted Cadillacs sticking end-first out of the ground. By the time you get to either Santa Monica, California or Chicago, Illinois—depending on which end of the route is your starting point—you’ll have seen enough to be able to dine out on your stories for years.
In general, the spring through fall months are best for traveling Route 66. It’s important to note that while many of the road trips listed below are clearly delineated from start to finish, Route 66 isn’t indicated as a single route on contemporary maps —so use a resource like Historic 66 to get turn-by-turn directions.
Pacific Coast Highway – San Luis Obispo to Monterey, California
Sweeping views from high above the blue-green Pacific Ocean make the Pacific Coast Highway (PCH) one of the most beautiful drives on Earth, not just in America. Ideal for the summer or fall, this epic route through Central California is only 150 miles long, but the sometimes slow-going adventure isn’t a trip you’d want to attempt in just one day.
Starting right after Carmel, the landscape becomes particularly dramatic as the road narrows and the views expand, and you’ll wind past a couple state parks worth a look: Point Lobos State Reserve is known for viewings of sea otters, seals, and whales, while Garrapata State Park is renowned for its redwood groves. Just south of Garrapta is the most photographed icon of the PCH, Bixby Bridge, one of the tallest single-span concrete arch bridges in the world.
From there, the largest concentration of stops are in and around the small town of Big Sur. Perched way atop the patio of the European-style Nepenthe cafe, you can enjoy a glass of wine with a breathtaking view over the Pacific, or you can grab a quick nosh at Big Sur Bakery before pausing at the McWay Falls overlook or taking a peek at the sunset through Keyhole Rock on Pfeiffer Beach.
Just past the southern end of Big Sur, the landmark not to miss is Hearst Castle, newspaper magnate Randolph William Hearst’s dazzling example of over-the-top, 1920s-style Spanish Colonial-Revival architecture—as well as home to a herd of grazing zebra. Set high above the coast, the estate is open to the public for hour-long tours that should ideally be reserved in advance.
Great River Road National Scenic Byway – Minnesota to Louisiana
What the Pacific Coast Highway is to the Pacific Ocean, the Great River Road is to the Mississippi River. Starting in Northern Minnesota, the Great River Road nearly spans the width of the U.S., stretching more than 2,000 miles and ending around New Orleans, Louisiana. Like Route 66, it’s not just one road, but rather a series of roads that follows the eastern and western sides of the Mississippi River through Wisconsin, Iowa, Illinois, Missouri, Kentucky, Tennessee, Arkansas, and Mississippi itself.
As a National Scenic Byway, each state along the Great River Road has its own interpretative center that helps educate travelers about the route’s history. In Mississippi you’ll find the Vicksburg National Military Park Visitor Center, in Missouri the Mark Twain Museum, and Iowa is home to the 200-mound-strong, prehistoric Effigy Mounds National Monument. Some of the many notable overlooks dotting the byway are found at Grandad Bluff and Buena Vista Park in Wisconsin, as well as the Chain of Rocks and Old Mississippi River Bridge in Missouri. Consider a fall or spring road trip for the best weather and the opportunity to avoid large amounts of other drivers.
Historic Route 1 – Maine to Florida
Beginning near the Canada border at Fort Kent, Maine, Historic Route 1 spans nearly 2,500 miles, unfurling along the Atlantic coast of New England, passing through a slew of east coast metros—including New York City, Philadelphia, Baltimore, and Washington, D.C.—and finally ending in Key West, Florida.
In New Hampshire, picnic on quiet beaches or stop into colonial towns such as 400-year-old, harborside Portsmouth, full of charming restaurants, inns and shops. Don’t miss Salem, Massachusetts, famous for its witch trials (and home to the Salem Witch Museum), and Newport, Rhode Island, known for historic-landmark mansions like The Breakers, the lavish summer “cottage” of Cornelius Vanderbilt II. In the South, Historic Route 1’s highlights include Northern Virginia’s Mount Vernon, once the home of George Washington; South Carolina’s 45,000-acre Carolina Sandhills National Wildlife Refuge; the sleepy Georgia coast; and the entire Atlantic coast of Florida.
If you’re starting this route in New England, consider driving in late September or early October for the fall colors—and when you don’t have to worry about getting snowed in.
Route 98 – Gulf Coast, Southern Florida to Mississippi
One of America’s oldest driving roads, Route 98 dates to 1933 and originally connected Pensacola and Apalachicola in Florida, but now runs from Southeast Florida to West Mississippi. While much of the Central Florida section is rural, what’s most interesting are the sections running parallel to the Gulf Coast; drive this during the spring and summer months and make sure you bring your bathing suit.
The coastal portion of Route 98 begins at the Florida Panhandle, where the Apalachicola National Forest offers numerous lakes, trout ponds, and on- and off-trail bicycling and hiking. Don’t drive through the small fishing town of Apalachicola without a stop for fresh-caught seafood, like the rich oysters at Hole In The Wall Seafood. Just west is St. Joseph Peninsula State Park, home to one of the highest-rated beaches in the U.S. due to miles of sugar-white sand, and continuing west are a number of larger, more well-known beach towns like Panama City and Pensacola, as well as Seaside, which served as the setting for The Truman Show. From here, before crossing Mississippi, the highway runs along the southern portion of Alabama, where a recommended detour is the national seashore of Orange Beach and Gulf Shores; if you’re lucky, you’ll spot some sea turtles here.
Acadia National Scenic Byway – Maine
Acadia National Scenic Byway could really be completed in a half-day, but it packs a lot into its 40 miles. Traveling through Acadia National Park, the journey starts at Route 3 just south of Trenton, crossing the bridge onto the 108-square-mile Mount Desert Island. From here, the views and drive become increasingly dramatic, with a craggy coastline reminiscent of California’s Pacific Coast Highway—but yet firmly rooted in New England.
The Byway’s highlights include Bass Harbor Head Light, a lighthouse that dates back to the mid-1800s, and Cadillac Mountain, the highest point in the park, but some of its most delightful features are interconnected carriage roads and old stone bridges, most of which are closed off to cars; to explore these areas, bring along your own bicycles, or rent them in the island’s ritzy seaside community of Bar Harbor. When you get hungry, enjoy fresh lobster at Bar Harbor’s Lazy Lobster or The Thirsty Whale. The summer months on the scenic byway can be very crowded, while the colorful foliage of the late fall (rather than earlier in the season) can offer gorgeous scenery with fewer tourists.
Columbia River Scenic Byway – Oregon
The first designated scenic highway in the U.S., the Columbia River Scenic Byway was begun back in 1913. Like the Acadia route, this drop-dead gorgeous 75-mile route—beginning just east of Portland in Troutdale and continuing onto The Dalles—could conceivably be driven in a day. Spring through fall are the best times to visit this heavily forested area, though fall will afford you the most colorful views.
The Byway is dotted with waterfalls, like Shepperd’s Dell and the impressive tall 620-feet-high Multnomah Falls, and scenic vistas include Chanticleer Point, one of the first you overlooks you’ll encounter traveling east, and Crown Point, one of the most photographed spots along the Columbia River. If time permits, stop at some of the historic landmarks along Lewis and Clark’s journey, such as Rooster Rock, Cascade Locks, or Rock Fort in The Dalles.
Blue Ridge Parkway’s Skyline Drive – Virginia and North Carolina
The entire Blue Ridge Parkway is a lovely 469 miles long, but its crown jewel is the 105-mile Skyline Drive. Running north-south along the crest of the Blue Ridge Mountains in Shenandoah National Park, Skyline Drive is accessible at four different entry points: Front Royal (north entrance) near Route 66 and 340; Thornton Gap at Route 211; Swift Run Gap at Route 33; and Rockfish Gap (south entrance) at Route 64 and Route 250.
The whole route can be driven in three hours, but with a speed limit of 35 mph and a whopping 75 overlooks, you’ll want to give yourself several more hours than that. Notable overlooks include Spitler Knoll, Range View, and Hogback, all of which offer unobstructed views across the Blue Ridge Mountains. A number of recreational areas dot Skyline Drive, including Big Meadows, where Franklin D. Roosevelt dedicated Shenandoah National Park and the Skyline Drive itself.
While late fall, winter, and early spring can make for undesirable weather and road conditions, September and October are best for seeing the fall foliage. If you start out early in the morning before the route gets busy, you’ll likely encounter wildlife like deer and black bears.
Going to the Sun Road – Glacier National Park, Montana
The 53-mile Going-to-the-Sun Road, the only road through the stunning Glacier National Park, is one of the most narrow and winding thoroughfares on this list, but rewards travelers with some of the most epic natural landscapes in the country. Gawk at actual glaciers from the Jackson Glacier Overlook and the route’s highest point, the 6,646-feet-tall Logan Pass, and see if you can spot the park’s resident white, fluffy mountain goats. The road also runs by several lakes, including Lake McDonald and Saint Mary, and majestic waterfalls like McDonald Falls (a couple miles west of Lake McDonald) and Bird Woman (located between Mounts Oberlin and Cannon).
The road’s accessibility is dependent on the amount of snow from the previous winter, usually opening by the first of June and staying open until October; the busiest traffic times are from late June through late August.
Hana Highway – Maui, Hawaii
On the island of Maui, the famous Hana Highway takes the best parts of Hawaii—beautiful beaches, sweeping ocean views, rugged hiking trails and lush tropical jungles—and arranges them along this singular, winding road. The 64-mile drive begins just east of Kahului Airport (OGG) in the laid-back surf town of Paia, before winding east along Maui’s north shore and way up into the hills.
Look for ocean rainbows over Ho’okipa, one of the most famous surf beaches on Maui, gape at the views from Wailua Overlook—a small turnout high above the Pacific Ocean—and enjoy the fact that many of the route’s spectacular waterfalls are set just a few hundred feet from the road. Some folks never make it past the small town of Hana (home to the luxurious Travaasa Hana, part of the iPrefer loyalty program), but you’ll want to continue on to the Kīpahulu District of Haleakalā National Park, home to the absolutely stunning Seven Sacred Pools and the waterfalls of ‘Ohe’o Gulch.
Maui is at its most rainy in the winter, when lush green foliage and powerful waterfalls only become more amazing. With mild temperatures year-round, there’s no bad time of year to drive the Road to Hana.
Before tackling any of these road trips, be sure to see these related TPG posts:
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