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A road trip is usually just as much about the journey as it is the destination. But you don't have to spend months planning a getaway to make it worth your while — even taking to the highway for just a couple of hours can completely change your point of view. Best of all, you’ll only need to fill the gas tank once for these five road trips from major U.S. cities. We’ve mapped out what to do when you get there.
Washington, D.C. to Richmond, Virginia (109 Miles)
DO: Before you decide that exchanging one city for another doesn’t feel like enough of a getaway, remember that Richmond’s nickname isn’t River City for nothing. Richmond was originally settled at the farthest navigable point up the James River before seafaring ships would hit waterfalls and rocks. Extending seven miles west from this point in the city center — known as the fall line — is a series of thrilling Class I to Class V whitewater rapids. Get in the water on a raft, tube, or kayak, or admire it from a distance by walking Richmond’s scenic riverside trails and picnicking at the Pony Pasture, a popular waterfront park.
EAT AND DRINK: Start the day with a cold-brew coffee and a breakfast pastry from Sub Rosa Bakery in the historic Church Hill neighborhood. If a picnic is in the plans, pick up a boxed lunch (with a cupcake) from Sally Bell’s Kitchen near the Museum District. Before dinner, enjoy a sunset cocktail at the rooftop bar at the art-forward Hotel Quirk downtown, or a beer on the deck at Hardywood Brewhouse and Tap Room in the Historic German Brewing District. For dinner, choose whichever fish is the freshest at acclaimed seafood restaurant Rappahannock in the city center.
STAY: The Graduate and the Quirk are both design-driven boutique hotels located downtown, with many attractions within walking distance. For a fancier stay, you can’t go wrong with the nearby Hotel Jefferson, an opulent 1895 grande dame.
Chicago, Illinois to Milwaukee, Wisconsin (92 Miles)
DO: In Milwaukee, your visit can be split between what one might consider high-brow and low-brow activities. Made famous by pre-craft beer brewing giants like Schlitz and Pabst, Milwaukee has now embraced the small-batch brewery movement, too. Beer connoisseurs can indulge in several tours and tastings at the city’s dozens of microbreweries. Elsewhere, the Harley-Davidson Museum documents the Milwaukee-based brand’s evolution and includes exhibits that may delight even non-Knuckleheads, who will want to make a detour to see the diamond-encrusted motorcycle. Or opt for art and architecture: The city’s skyline was transformed when the Santiago Calatrava-designed pavilion of the Milwaukee Art Museum opened in 2001. The building’s exterior is notable for a winglike shade that spreads its individual steel “feathers” to allow sun into the space. It folds back together when the museum closes (or when winds are stronger than 23 mph). Calatrava’s fantastic lakeside structure holds many of the museum’s impressive 25,000 works of art.
EAT AND DRINK: You can’t go wrong with Breakfast at Fuel Cafe in Walker’s Point, but if you want the full Wisconsin experience, order a bloody mary garnished with cheese curds alongside your hot chicken and French toast plate. For lunch, Milwaukee Public Market in the artsy Third Ward neighborhood is ground zero for tasting local cheese and brats, but the plethora of other options means everyone will find something delicious. Egg & Flour Pasta Bar on the East Side is relatively new, but the pappardelle Bolognese will be a dish you remember long after leaving.
STAY: The Saint Kate has original art in the guest rooms, lobby, and multiple gallery spaces — not to mention a blackbox theater and live music. It should be at the top of your list.
Los Angeles, California to Carlsbad, California (87 Miles)
DO: Carlsbad is a beach town first and foremost, built on the cliffs beside a gorgeous stretch of sandy Pacific coastline. So predictably, the beach should be your first stop — and South Carlsbad State Beach is a local favorite. If you have time to delve into another side of SoCal culture, however, take the self-guided walking tour at Carrillo Ranch, the historic ranch and hacienda that actor-turned-conservationist Leo Carrillo built in the hills about 10 miles outside of town. Spend a few hours amid the charming and rustic ranch buildings, wandering peacocks, shady paths, sun-bleached corrals, and pastures to imagine a California before freeways and green juice.
EAT AND DRINK: Caffeinate with the surfers by getting a table at Cafe Elysa. (And if you want to join them in the waves after, note that surfing is an intensely physical activity that will surely burn off all the calories in the cafe’s excellent stuffed French toast.) But you may want to save room for dessert after lunch at the Village Kitchen and Pie Shoppe, an old-school coffee shop with pies displayed in a glass-front refrigerator. If you plan ahead, you can book a dinner at Campfire, a beautiful space with a kitchen that has a way with fire — the charcoal-roasted broccoli is an appetizer that you’ll dream about for months to come.
STAY: While the Carlsbad flavor you’ll get from an oceanfront room at the beachy (but pricey) Beach Terrace Inn is hard to top, the town also has several decent chain hotel options, so now may be the time to leverage those hotel loyalty points.
Seattle, Washington to Astoria, Oregon (181 Miles)
DO: Blessed with a spectacular setting on a steep hill above the mouth of the Columbia River, Astoria handily balances the gritty funk of a port city with some serious small-town charm. In addition to serving the fishing and timber industries that kept the waterfront busy, this town was at the forefront of several important historical events. Nearby is Fort Clatsop, the endpoint of Lewis and Clark's famous expedition, where the explorers replenished their stores for the trip back east in 1805. The city also played a starring role in the classic movie The Goonies. You may recognize some of the Victorian houses and storefronts in the downtown area, and you can indulge your inner film fan with a self-guided Goonies tour. Finally, walking at least a segment of the Riverwalk is an enjoyable way to gain a quick understanding of the town’s vibe — a little hippieish, a little outdoorsy, a little old-fashioned, but always tied to the water.
EAT AND DRINK: With the Pacific glinting in the sunlight right down the hill, you can expect the local cuisine to be fish-focused. Grab breakfast where cannery workers used to stop before their shift at Coffee Girl, or if it’s Sunday, pick something up at the Astoria Sunday Market. Lunch at South Bay Wild is one way to know that you’re eating local — the restaurant itself is part of the seafood market. Choose between a stellar fish and chips platter or a seafood banh mi. Finish the day with dinner and drinks at the Sasquatch Sandwich food trucks, parked at 1343 Duane Street next to Reach Break Brewery and Reveille Ciderworks. The Fort George Brewery, located in a massive former car dealership, is a favorite stop, too.
Boston, Massachusetts to Portland, Maine (112 Miles)
DO: Getting oriented to this sea-faring town is best done on the water. Hop the ferry to Peaks Island (less than an hour round-trip) and observe the city as it’s been seen by centuries’ worth of fishing boats. While harbor seals play around the ferry, take in the skyline, punctuated by the Observatory Tower, a few tall downtown buildings, restored warehouses at the Old Port, Victorian houses lording over hilly neighborhoods, and several church steeples. Back in town, use your time to experience Portland’s greatest hits: a climb up the Observatory Tower, a stroll and a picnic along the Eastern Promenade, and a trip to the Portland Museum of Art to see the collection of local hero Winslow Homer. Don’t skip a walk through Portland’s impossibly charming Old Port district; among its cobbled streets, you can find some stylish housewares and clothing stores.
EAT AND DRINK: Doughnuts are a big deal in Maine. The delicious dunkers at Holy Donut are made from local potato flour and come in Portland-friendly flavors like blueberry lemon and maple. The city has many worthwhile restaurants, but the poutine at Duckfat and a small-plate dinner at Central Provisions (with someone who likes to share) should not be missed.
STAY: The Press Hotel is a trendy 110-room hotel repurposed from downtown’s old Portland Press Herald Building. The typewriters and printing-press hardware used as artwork, along with literary-chic guest-room decor, are a nod to the building’s past.