Fall Bike Rides from Waynesboro, VA

Luxury Cabins at Iris Inn

Helmet…check. Spare tubes…check. Sense of adventure…check. If you’re looking for a bicycling destination that offers a variety of picturesque landscapes and delectable wayside stops, pack your gear and head to the Shenandoah Valley. With Waynesboro, Virginia, as your base camp, you’ll have an abundance of on-road and off-road routes to choose from, taking you everywhere from the peaks of the Blue Ridge Mountains to the historic towns nestled below. Start your adventure rested and well-fed with a night at the Belle Hearth Bed & Breakfast or the bike-friendly Iris Inn, then spend your day exploring one of these suggestions.

Sample the Fruits (and Grains) of the Valley

Flying Fox Vineyard

This Waynesboro to Nellysford loop will bring you past some of our region’s delicious offerings. You’ll find stunning views and wines at Veritas Vineyard and Winery, internationally acclaimed craft spirits at Silverback Distillery, and cold taps at Wild Wolf Brewing Company.   Wild Wolf’s farm-to-fork restaurant makes this the perfect rest stop on your tour. Refreshed, pedal south to Flying Fox Vineyard to sample one of their Virginia Vermouths or premium wines. And no Nellysford loop would be complete without a stop at Bold Rock Hard Cider! For an abundance of additional grain, grape, berry, and fruit adult beverage options on your route, be sure to check out this map.

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Two-Wheeled Touring Near Waynesboro – Bicycle and Motorcycle Itineraries

Sometimes the ride is as exhilarating and beautiful as any destination. If you’re looking for sweeping turns, windswept mountain vistas, or country roads to cruise, these bicycle and motorcycle itineraries are sure to inspire.

Pedaling on Pavement

Day Trip Tours from Waynesboro are plentiful. Beginners and family-friendly options include the South River Greenway, stretching from Constitution Park and meandering along the South River, which on Saturday mornings features the Waynesboro Farmers Market. Or stretch a little further with the 12.5 mile Waynesboro-to-Dooms Day Loop, which takes you along the South River as it flows north towards its confluence with the North River. Intermediate riders may love the Waynesboro-to-Grottoes Loop which, over the course of 35 miles, can include a tour of Grand Caverns in the town of Grottoes and passes the renowned horticulturalist André Viette’s extensive perennial garden and nursery on Long Meadow Road.  Don’t be shy about exploring other options, as Bike the Valley’s database of On Road rides remains extensive.

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