By Michael Ream
Warmer weather brings with it an impulse to hit the highways and byways, seeking out both the iconic and unique in roadside fun. Major cities in the U.S. are just a day’s drive from some interesting things to see, places to soak up a full range of Americana, and dine on some creative cooking before settling in for the night at cozy lodgings. We’ve taken stock of some great drives you can make from New York, Los Angeles, Chicago, and other cities. Here are our picks for where to find summer fun on the road.
New York: Heading up the Hudson
The Route: Amidst the striking scenery and creeping exurbia of the Hudson River Valley, day-trippers and more leisurely travelers can discover history and handsome old homes in the picturesque villages off of U.S. 9, beginning with Sunnyside in Tarrytown, the home of author Washington Irving.
Stroll along the nearby Croton Aqueduct Trail, a verdant stretch of path, to reach Lyndhurst, a fine example of a 19th century Gothic Revival mansion. Farther north is the evocatively named Sleepy Hollow, setting for some of Irving’s best known stories and Hyde Park, with a cluster of sights dedicated to the Roosevelts and Vanderbilts. Keep heading north to Rhinebeck, which has a quaint downtown with interesting shops and restaurants, and an aviation museum in a historic aerodome that’s a hit with young and old alike.
Cross the Hudson and head west along NY 28 as it winds through the Catskill Mountains. A few miles past the entrance to Catskill Park stands the town of Woodstock, a laid-back artists’ colony and namesake of the series of rock music festivals (the original concert was actually held some 50 miles away).
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The scenery grows more rustic as you go, passing steep ravines and a longtime ski hill. Circumnavigate the park then swing onto NY 17 to head south, passing more ski hills on the way to Port Jervis, a weathered city at the juncture of New York, New Jersey, and Pennsylvania that was a historic crossroads for river, rail, and road traffic. From here, it’s just a short drive back to New York City.
Where to Stay: The Rhinecliff is a refurbished historic hotel perched on the banks of the Hudson just outside Rhinebeck (nightly rate from$199-$259) Spacious, airy rooms, all with king beds, are full of country charm, and include modern touches like flat screen televisions and Internet access, as well as sweeping views of the surrounding countryside (Each of the nine rooms has a private balcony, which is a lovely place to sit on sunny days). The hotel’s restaurant is appealingly rustic, with a menu that features local ingredients.
Where to Eat: While it’s a bit out of the way, nestled in the mountain hamlet of Preston Hollow, several miles outside Catskill Park, the Bees Knees Cafe is worth the trip for its modern take on country cooking. Lunches are served al fresco on weekends only from Memorial Day weekend to Columbus Day, with a changing menu of dishes created from locally raised meats, cheeses, and produce, including delicious desserts.
Insider’s Tip: If you’re planning on doing some hiking in Catskill Park, fuel up first at Sweet Sue’s. Located in the town of Phoenicia near the heart of the park, it has a smorgasbord of pancake options and to-die-for French toast made with banana bread. Real maple syrup on offer, too.
Los Angeles: Cruising the Pacific Coast
California’s U.S. 1 is one of the world’s more iconic roadways: for much of its length between Los Angeles and San Francisco, it lazily winds its way along cliffs high above sparkling ocean waters, with some nice stopping off points sprinkled among the rugged landscape like diamonds in the rough.
Flee the smog of LA, zip past Santa Barbara (stopping for a look at the Funk Zone), and the faux-European style of Solvang (slowing down to smell the Lily Bee Lavender Farm as you pass), skirting vineyards and the southern reaches of the west coast’s great agricultural empire, with a cornucopia of produce. Check out the kitsch overload at the Madonna Inn in San Luis Obispo, then chow down on some fresh seafood in Morro Bay.
At San Simeon, luxuriate in the Xanadu-like splendor of Hearst Castle, which towers majestically over the Pacific. The nearby town of Cambria is known as a funky little artists’ village, with many galleries and boutiques. Keep pushing ahead—you still have a couple hours to go to reach Big Sur, with its towering Redwood trees and breathtaking mountain vistas emerging from ocean-side fog that have inspired many artists, writers, and other creative souls.
Tool on up to the Monterrey peninsula, home to some of America’s more evocative sounding towns, such as Carmel and Pebble Beach, as well as the scenic Seventeen Mile Drive. Scooting east to U.S. 101 will bring you back to the city of angels in a fraction of the time it took on the coast, albeit through much less interesting surroundings.
Where to Stay: A legend among generations of seekers, hippies, and others drawn to Big Sur, Deetjen’s Big Sur Inn (rooms and cabins run from $90 to $250) includes a collection of spartan cabins dropped in a canyon amongst the Redwoods. Luxury lodging it isn’t, but if you’re looking for the mystical, intangible vibe of Big Sur, this is the place.
Where to Eat: While a plethora of restaurants can be found in the towns that dot the coast, serving everything from standard Mexican fare to more innovative preparations, longstanding favorite Buona Tavola in the center of San Luis Obispo, stands out for its classic Northern Italian cooking. All the old favorites are here, and there’s also a location in Paso Robles.
Insider’s Tip: The Santa Maria Valley is known for its barbecue, with succulent, smoky smells wafting from hickory pits in San Luis Obispo and other towns. You can pick up some ‘cue everywhere from roadside shacks to sit-down restaurants. Even the venerable Santa Maria Inn, a historic hotel located in the town of the same name, offers Santa Maria Tri-Tip, a local specialty.
Chicago: A Great Lakes Getaway
The only one of the Great Lakes that lies entirely within the United States, Lake Michigan’s long shoreline is dotted with both bustling urban areas like Chicago, as well as charming smaller communities in Michigan and Wisconsin. Marked with lighthouses that attest to the region’s long maritime history, these towns are home to quaint shops, hometown diners serving up blue plate specials, and a relaxed, friendly air.
Skirting the southern edge of the lake, take the Chicago Skyway as it soars over the old steel mills of the city and neighboring Gary, Indiana. Just as you cross into Michigan, you reach New Buffalo, the best of a cluster of beachside towns that have become prime real estate for Chicagoans’ second homes. Boating and cycling are popular here, as is hang gliding off the nearby sand dunes, and even lake surfing!
Fruits and flowers burst out from the fields outside the old twin lake cities of Benton Harbor and St. Joseph, while a little farther along the shoreline, South Haven has a historic downtown with a popular maritime museum. Shopaholics will want to stop in Saugatuck, which has a wide selection of boutiques and galleries. Holland is a picturesque town with old world touches, including yummy Dutch baked goods, and Grand Haven may have the nicest beach on the entire lake, with a wide strip of powdery white sand opening onto the inviting waters.
At Muskegon you can pick up a car ferry and cross the lake to Milwaukee, historic heart of beer making and home of fine museums and excellent ethnic food. It’s worth making a short side trip north to Sheboygan to see the American Club, a grand old resort with a fascinating history, before heading south back to the windy city.
Where to Stay: The Boulevard Hotel & Bistro in St. Joseph (rates from $130-$470) has stylish rooms, all suites, with contemporary furnishings. Some overlook sunsets on Lake Michigan. The bistro is renowned for its delicious meals featuring fresh ingredients, and an extensive wine list.
Where to Eat: Located in a converted general store in downtown Holland, Alpen Rose Restaurant & Cafe is a cozy spot with a contemporary continental menu that includes offerings like pork Provencal and Tuscan lamb, as well as local seafood favorites like Great Lakes perch. One of their imaginative cocktails is a nice start to the evening, and there’s a good wine list, too.
Insider’s Tip: To really get a sense of Holland’s Dutch heritage, visit during the town’s annual Tulip Time festival (held mid-May). Classic small town fun, the weeklong party provides a look at traditional culture from the Netherlands, with parades, Dutch dancers and other entertainment, amidst a sea of brilliantly colored blooms.
Portland: Puttering along the Pacific
U.S. 101 clings to the top of cliffs looming over the Pacific Ocean as it shoots down through thick stands of trees that line the Oregon coast. Every few miles, another town emerges from the forest, including pleasant roadside stopovers that manage to combine the hardiest traditions of the Pacific Northwest with a taste of the region’s open-minded attitude. You can’t expect to go anywhere too fast, but that’s part of the fun of this trip; it’s all about the drive itself, which also makes it a nice scenic detour for those travelers heading down from Seattle and Vancouver.
Begin your adventure in Astoria, near the northwestern tip of Oregon. The first permanent American settlement in the Pacific Northwest and the oldest U.S. city west of the Rocky Mountains, the town is stocked with historic homes and is known for its scenic views.
More history is found at nearby Fort Stevens State Park and Fort Clatsop National Memorial Park, the latter of which features a replica of a fort used by the Lewis and Clark Corps of Discovery. Heading south, you may want to stop by Cannon Beach, which lures in throngs of weekenders and outdoor recreation fans, or press ahead to Tillamook, famous for its cheese, with the eponymous cheese factory offering tours to visitors.
The highway curves inland from the waters of Tillamook Bay. Some 50 miles farther, you come to Depoe Bay, a mecca for whale watching. Just a little farther south is Newport, a honkytonk town home to both the Oregon Coast Aquarium, with an impressive collection of maritime species and the Hatfield Marine Science Center, with plenty of fascinating exhibits.
From Newport, head east to Corvallis and then I-5, which completes the loop back to Portland.
Where to Stay: Perfect for a couple’s getaway, the Channel House (rates from $100 to $330) in Depoe Bay has magnificent views overlooking the ocean and craggy coastline. Several rooms have windows facing the ocean and even include binoculars to help you spot whales. Go ahead and splurge for a room with a private outdoor whirlpool.
Where to Eat: You’ll find lots of fresh seafood places along the coast, but for a truly memorable meal, head for the Bay House in Lincoln City. The longtime favorite has a changing menu that includes a nightly tasting, with samples of some of the chef’s creations, as well as entrees that run the gamut from Oregon quail to ingenious fish preparations. Enjoy your meal amid the views of surrounding woods and waters.
Insider’s Tip: Beer lovers should definitely make a stop at the Rogue Ale Brewery in Newport. The award-winning brewery includes an on-site pub, where visitors can sample the wide variety of suds.
Miami: Tropical Treasures in the Keys
Stretching into the Gulf of Mexico and the Atlantic Ocean like an old fishing line, the Florida Keys are a world unto themselves. The string of small islands (from the Spanish "cayos") is the sort of place where many go to escape from the pressures of the world, whether for a weekend or a lifetime.
A mélange of cultures sizzles together under the brilliant blue sky and tropical sun, with backwoods Florida smashing headfirst into Caribbean cool, all pervaded with a decidedly hedonistic air (Jimmy Buffet got his start around these parts, and Ernest Hemingway was a well-known regular). Kick back beside the cool sea waters, crack open a cold one, and salute one of the funkiest places to travel in the United States, if not the world.
Get the party started just south of Miami in Homestead, where you’ll find one of the more oddball tourist attractions around: the Coral Castle sits right along the highway, a testament to one man’s dedication and determination. Ed Leedskalnin carved an entire grand edifice out of coral, including coral furniture! Wander around to see some of the castle’s many unique features.
Homestead is also the jumping-off spot to Everglades National Park, with over one million acres of subtropical landscape and hundreds of species of birds and wildlife. You can spot gators from the park’s visitor center, where there are several walking trails.
Not long after leaving Homestead, you hit the keys, beginning with Key Largo, which is an overdeveloped tourist town, but does give you your first chance to sample some Key Lime Pie, as well as tons of watersports. Fantastic sport-fishing can be found in nearby Islamorada, site of one of the most powerful hurricanes to ever hit the United States, in 1935.
You have now been driving for many miles along the Overseas Highway, which wiggles along between sea and sky, passing through mangrove swamps and pockets of nature that have managed to resist tourist-oriented development. The road follows the route of the old Florida and East Coast Railway, and offers some outstanding views, with some of the most spectacular found on the Seven Mile Bridge, south of Marathon.
The old Seven Mile Bridge runs parallel to the new one for a few miles. Closed to motor vehicles, it is a popular spot for strolling and fishing, and connects to Pigeon Key a few miles to the west, which gives a sense of the old ways of the keys: it was a work camp for railroad workers, and has a museum dedicated to area history as well as its own laid-back beach that’s a nice spot for snorkeling or picnicking.
By now, you’re probably ready to get to Key West. This last chance outpost emanates a raffish air, with all sorts of bawdy drinking dens and nightlife spots. There is so much weirdness to soak up here, a short trip almost does not do it justice; some people roll into town and never leave. Still, it’s worth checking out the Ernest Hemingway Home to learn about one of Key West’s (many) famous residents and Fort Zachary Taylor Historic State Park for beach fun, as well as the nightly sunset celebration at Mallory Square Dock.
Where to Stay: There are so many places to stay in the keys that finding the perfect spot isn’t as hard as you think. Still, Hawk’s Cay Resort, (rates from $325-$600) located on tiny Duck Key, offers so many amenities and activities it’s hard to go wrong: all sorts of water activities are available, including swimming with dolphins, and the resort offers five breathtaking pools and its own saltwater lagoon.
Where to Eat: Keep your eyes peeled for mile marker 47.5 for the Seven Mile Grill, near the bridge. This no-frills throwback is a taste of old-school keys cooking, with all sorts of grilled and fried fish on the menu; some of it freshly caught. Have a bowl of conch chowder or shrimp bisque, and don’t forget the Key Lime Pie.
Insider’s Tip: For a look at how the original inhabitants of Florida lived, swing by Miccosukee Indian Village, just north of Everglades National Park, where you can view native crafts and see live alligator demonstrations. Historically a part of the Seminole nation, the tribe has prospered thanks to gaming and other tourism services.
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Michael Ream is the author of Backroads & Byways of Iowa, Best Hikes Near Madison, and three other travel books. He has contributed to numerous other guidebooks and magazines and has chased stories across three continents, but always comes home to the Midwest.
Photo Credits: New York: Hyde Park via Shutterstock.com; Los Angeles: Robert Holmes/CalTour; Chicago: Benton Harbor via Shutterstock.com; Portland: Cannon Beach via Shutterstock.com; Miami: Everglades National Park via Shutterstock.com