New Paltz, New York

Just a 90-minute drive or train ride from New York City, this Hudson Valley college town is a magnet for athletes and outdoor enthusiasts.

Swim Here

Tucked in the Minnewaska State Park Preserve, the secluded, spring-fed Lake Awosting is perfect for open-water practice. (Note: swimming is permitted in the roped-off area between 11 a.m. and 5:30 p.m. when lifeguards are on duty.)

Bike Here

Covering 32 miles and 3,200 feet of climbing, the Great Shawangunk Hill Loop (extending from downtown New Paltz into Ulster County and back) is as scenic as it is challenging.

Run Here

From downtown New Paltz, hop on the Wallkill Valley rail trail, a quiet, shaded, and soft-surfaced stretch of some 21 miles between the towns of Gardiner and Kingston.

Race Here

Complete the grueling bucket-list eight-stage Survival of the Shawangunks (SOS) Triathlon (usually held in New Paltz each September) and earn bragging rights forever.

Explore Here

Hike up to Skytop Tower at the peak of the Mohonk Preserve, for sweeping views of the Catskill mountains—and to spot six states (New York, New Jersey, Connecticut, Massachusetts, Pennsylvania, and Vermont) in the distance.

Stay Here

Built in 1869 to resemble a Victorian castle, the Mohonk Mountain House is a throwback to a bygone era of opulence and luxury—rooms feature wood-burning fireplaces and views of the surrounding Hudson Valley.

Eat Here

Named after the Grateful Dead song, the quirky Mexicali Blue in downtown New Paltz has a funky hippie vibe—and a short-rib burrito that was recently voted one of the best in the nation.

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Roanoke, Virginia

Nestled in the Blue Ridge Mountains and saturated with trails and hilly climbs, this eclectic town is an easy drive from both Richmond, Virginia, and the Washington, D.C./Baltimore metro area.

Swim Here

About 35 miles outside the city, Smith Mountain Lake—the second largest freshwater lake in Virginia—is a popular swimming spot and has served as the site of the East Coast Open Water Championships.

Bike Here

Known as “America’s Favorite Drive,” the Blue Ridge Parkway is a mecca for cyclists. Some 80 miles of the byway winds through the lush Roanoke Valley, with access to the parkway roughly five miles from downtown.

Run Here

The Roanoke River Greenway offers a nearly-continuous paved route for 30 miles—almost 10 miles within city limits. Seeking a softer surface? Head to Carvins Cove Natural Reserve to access 60 miles of forested trails.

Race Here

Roanoke is one of the latest additions to the Ironman 70.3 roster (race date: June 6, 2021); or check out the annual Foot Levelers Blue Ridge Marathon, held in April and dubbed “America’s Toughest” for its relentlessly hilly course.

Explore Here

Bike or run up to the top of Mill Mountain (a preferred route of the Roanoke Tri Club) and soak in the views of the sprawling valley below. Make sure to snap a selfie in front of the famed Roanoke Star, the “Hollywood sign of the East Coast”—and the world’s largest freestanding illuminated man-made star.

Stay Here

Now run by Hilton, the stately Hotel Roanoke was built in 1892 to accommodate guests who flocked to the city after the completion of the Northern and Western Railroad. Despite its antique aesthetic, the hotel’s recently-renovated interior is still decidedly modern.

Eat Here

Extremely walkable, Roanoke is crammed with cuisine options. Local Roots is a foodie favorite for its fresh and organic seasonal menu, all sourced from farms around southwest Virginia.

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Sonoma County, California

About a two-hour drive from San Francisco, the pastoral countryside found along California’s coastal foothills is ideal territory for triathletes and wine lovers.

Swim Here

Jump into Geyserville’s Lake Sonoma, a 2,700-acre reservoir with 50 miles of coastline surrounded by oak forests and meadows. Yorty Creek (on the north side of the lake) is a designated swim beach, but access is allowed wherever there’s safe entry.

Bike Here

The roads through wine country tick all the boxes: rolling terrain, breathtaking scenery, and proximity to vineyards. Go-to routes for local cyclists include Red Winery Road (between Healdsburg and Geyserville) and the 30-mile Dry Creek Valley and Alexander Valley loop (starting and ending in Healdsburg).

Run Here

Sonoma County is rife with runner-friendly trails with epic views, including the partly-paved Santa Rosa Creek Trail (accessible from downtown Santa Rosa) and the streamside Valley of the Moon trail in Sonoma Valley Regional Park.

Race Here

Both the full- and half-distance Ironman Santa Rosa events typically draw big crowds every July and May respectively, while the Sonoma Women’s Tri (July) is a beginner-friendly option.

Explore Here

The coastal town of Bodega Bay is prime for wildlife spotting. Bring binoculars and look for whales, seals, bald eagles, and blue herons. You can also squeeze a wetsuit-clad swim in at Doran Park Beach, a sheltered two-mile stretch with gentle surf and chilly water.

Stay Here

Aside from its chic mid-century modern flair, the Astro in downtown Santa Rosa stands out for its devotion to cyclists: The staff is equipped to assemble and make basic bike repairs.

Eat Here

Hit up Pizzando in Healdsburg for its daily “Pies and Pints” happy hour, a special including a wood-fired pizza and a pint of craft beers. For $15, it’s the tastiest deal in town.