5 Road Trip Ideas

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Whether you like to travel near or far, domestic travel closer to home may be the first opportunity we have to venture out. Short road trips might be the perfect stepping stone to ease your way back into the groove.

These five trip ideas from around the country have a little something for everyone. If your miles and points have been a burning hole in your pocket, there are plenty of earning and redemption opportunities to keep your journey affordable and luxurious, too.

1. Explore the Finger Lakes and Catskills

With 11 lakes and ample scenery, the Finger Lakes region is a great option to escape urban centers and explore New York state’s rolling countryside. Depending upon where you begin your journey, you can choose from a variety of road trips.

Less than five hours’ drive from New York City, Aurora and Cayuga Lake offer a great place to disconnect and destress. Inns of Aurora (five individual inns) provides a calendar of activities including yoga, kayaking and contactless painting workshops.

The Fairfield Inn & Suites Geneva Finger Lakes, a Marriott Bonvoy property where a free night ranges between 22,000 and 30,000 points, is about two miles from lakefront Belhurst Castle and Winery (which also has its own lodging options).

A shorter drive from New York City (two and a half hours) are the Catskill Mountains. Visit independently or as part of a circle itinerary including the Finger Lakes.

The Roxbury at Stratton Falls is a great place for those seeking to commune with nature, thanks to opportunities for hiking and picnics, especially with its private waterfall trail. The hotel offers entertaining accommodations with cottages based on different themes like superheroes and Cinderella’s fairytale gown.

2. Drive Appalachia

For hikers, the Appalachian Trail begins as far north as Maine and descends through Georgia. Mid-Atlantic travelers may want to consider driving through this culturally rich region, especially the short stretch between Pennsylvania’s Amish Country and North Carolina’s Blue Ridge Mountains. While the fall offers colorful scenery with changing leaves, spring and summer can be just as engaging in other ways.

If you drive from Lancaster, Pennsylvania, to Asheville, North Carolina, it should take roughly nine hours. Plan stops according to your personal interests, which might include:

  • Amish Country in Lancaster County, Pennsylvania.

  • Hersheypark near Harrisburg, Pennsylvania.

  • Baltimore, Maryland.

  • Shenandoah National Park in Virginia.

  • Charlottesville, Virginia.

  • Bristol, Virginia.

  • Asheville, North Carolina.

Fire up your hotel apps to find your favorite brands. Hotel Hershey, a Historic Hotels of America member, is the most famous, but a few others may be a good fit for points fans. The Courtyard Hershey Chocolate Avenue is available for 32,000 to 40,000 Marriott points per night, and Tru by Hilton Hershey Chocolate Avenue participates in Hilton Honors, which has a varying points price depending upon the night.

As you head farther south, there are plenty of places worth stopping. In Bristol, Virgina (said to be the birthplace of country music), The Bristol Hotel serves up great craft cocktails on the rooftop. Asheville’s Foundry Hotel, a Curio Collection by Hilton property, is located downtown and could be the ideal way to end a road trip — it is within walking distance of numerous bars, breweries and restaurants. Hilton Honors has dynamic pricing, meaning that redemption amounts will vary.

3. South Dakota

This state has plenty of spread-out attractions that mix urban life with natural splendor. It’s a great drive for families, too. Start in downtown Sioux Falls with a visit to the Kirby Science Discovery Center at the Washington Pavilion. Get your fill of city life here with great restaurants, bars and shopping.

The Holiday Inn Sioux Falls-City Centre is within walking distance of all downtown attractions. It generally costs around 30,000 IHG Rewards Club points per night here.

Leaving town, drive toward Chamberlain (Lewis and Clarke-style), where you can see the famous Dignity of Earth and Sky statue honoring the state’s Native American population. This is almost halfway to Rapid City, the next stop of the trip.

Mount Rushmore National Memorial is the must-see on this road trip, but save time for Badlands National Park. Both can be explored while using Rapid City as a base.

A little farther west, Crazy Horse Memorial is a popular stop where visitors can learn more about the Native American populations. This is an easy day trip from Rapid City.

4. Portland to Southern Oregon

Great coffee, craft cocktails, an epic food truck scene and eclectic shopping make Portland, Oregon, a great place to begin or end a road trip.

Portland has plenty of great hotels to choose from including well-known The Nines, A Luxury Collection Hotel downtown and the new Hyatt Regency Portland at the Oregon Convention Center, which had its grand opening this year.

The Nines is a Marriott Bonvoy hotel requiring between 40,000 and 60,000 points per night; the new Hyatt Regency is a World of Hyatt Category 3 hotel requiring 9,000 to 15,000 points per night.

Leaving Portland, drive south making stops in Salem, the state capital, and Eugene at the southern end of Willamette Valley (known for many of Oregon’s great wines). Keep heading south toward Crater Lake to join the Rogue-Umpqua Scenic Byway, often dubbed the “Highway of Waterfalls” that takes you through Umpqua National Forest.

Seasonal Crater Lake Lodge is a great home base when visiting Crater Lake National Park. Another great drive is along the Volcanic Legacy Scenic Byway showing off the dramatic landscape formed from the area’s volcanic activity. Don’t miss these tips for saving cash when visiting a national park.

Additional lodging options include the Ashland Springs Hotel and Ashland Hills Hotel & Suites. Both are part of Stash Hotels Rewards, a program designed for independent hotels where you can earn and redeem points for a free night. They are about one and a half hours from Crater Lake National Park.

5. California’s Highway 1

This is a great family trip, especially for those starting north of San Francisco and heading down to San Diego (or vice versa). Some of Highway 1’s most scenic stretches are within San Luis Obispo County, often called SLO, thanks to 100 miles of Pacific coastline (much of it protected). It is also home to one of the only drivable beaches in the state.

This road trip takes travelers to 13 state parks, numerous beachfront vineyards and National Historic Landmark Hearst Castle. There are lots of places to stay at the major cities and scenic towns along Highway 1, with some true standouts.

Vespera ON OCEAN, An Autograph Collection property along Pismo Beach is a Marriott Bonvoy Category 6 property. One night ranges in price from 40,000 to 60,000 points. Another option is Ventana Big Sur, an Alila Resort, in Monterey County. Alila participates in World of Hyatt as a Category 8 hotel, which prices at 35,000 to 45,000 points per night.

Photos courtesy of Visit Finger Lakes, Quirk Hotel Charlottesville, the South Dakota Department of Tourism, Travel Southern Oregon, Visit SLO CAL and Vespera ON OCEAN.


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