Connecting green spaces with urban trails to bring more natural beauty to U.S. cities isn’t new: Landscape architect Frederick Law Olmsted pioneered the concept in the 1860s when he designed Boston’s now-legendary Emerald Necklace. The revolutionary system used landscaped “greenways” to link 1,100 acres of metropolitan parks across 7 miles and 16 neighborhoods.
The idea has since become a fixture of urban hubs across the nation. And Virginia cities are no exception. Many now boast robust greenway networks—the Roanoke Valley, for instance, is home to a whopping 400 miles of interconnected trails.
The routes make it easy for bike-loving visitors to plan scenic tours that pair rare city views with convenient eats, drinks, and stays at cosmopolitan hotspots. Here we bring you an inside guide to four of the Commonwealth’s best.
Harrisonburg
The East Coast’s largest bike club has spent the past few decades transforming this small Shenandoah Valley city into one of the state’s most pedal-friendly destinations. Rocktown now boasts a rapidly expanding 16-mile network of dedicated greenways with plentiful views of peaks in the surrounding Massanutten and Shenandoah Mountain ridgelines.
Parks & Trails
The 2-mile-long Friendly City Trail is Harrisonburg’s flagship greenway system and acts as a springboard for exploring routes in parks in the city’s westside. The paved, landscaped path begins at Bluestone Elementary and winds through woodlands on the outskirts of municipally owned Heritage Oaks Golf Course before passing into 74-acre Hillendale Park. There you’ll find 4 miles of easy off-road riding and another mile-and-a-half of paved or crushed gravel trail. Combine Let It Flow and Hillendale Walking Trail for a gorgeous, 2.7-mile trip around the park. Then finish the ride downtown with a jaunt through 48-acre Westover Park.
The mile-long Blue Stone Trail, meanwhile, meanders north through playing fields and rec areas in and around 67-acre Purcell Park on the southside of town. A paved, mile-long connector by Newman Lake and James Madison University’s Hartman Hall brings access to the Edith J. Carrier Arboretum and Botanical Garden. Explore the picturesque, 125-acre complex of gardens, waterways, wildflower meadows, and century-plus-old forests via a 3-mile network of trails.
Get more info from Harrisonburg Parks & Rec: HarrisonburgVa.gov/Biking-Walking-Paths
Harrisonburg’s Friendly City Trail. Photos by Kyle Laferriere | Harrisonburg Tourism
Eat • Drink • Stay
The Side Of The Road Inn’s four-suite central manor house dates to 1790 and centers an elegantly landscaped, 8-acre property a half-mile from Bluestone Elementary. Spring for the luxuriously outfitted River Birch Cabin, a two-story brick cottage with exposed beams and a stone foundation from 1789. ByTheSideOfTheRoad.com
Indulge in superlative small-batch heirloom ciders in a hip and funky downtown tasting room at Sage Bird, about a mile from Friendly City Trail’s northern terminus. SageBirdCiderWorks.com
Craft beer lovers should stop at nearby Restless Moons Brewing to sample an ever-rotating menu of about a dozen small-batch beers. RestlessMoons.com
Local Chop & Grill House offers regionally sourced, New American steakhouse cuisine in a thoughtfully overhauled historic warehouse just up the street. Don’t miss the cozy bar area and its formidable menu of craft cocktails. LocalChops.com
Roanoke
Sandwiched between the Blue Ridge Mountains to the east and the Alleghenies to the west, the Star City has gained a reputation in recent years as one of the East Coast’s top hubs for outdoor recreation—and its 30-plus-mile greenway network has much to do with the accolades.
Parks & Trails
Municipal trails sprawl outward in nearly every direction from a downtown area brimming with restaurants, breweries, and bars. The system’s backbone route, the 14.2-mile Roanoke River Greenway, passes east and west through a chain of riverside parks and green spaces near historic neighborhoods like Grandin Village, which is chock-full of 19th and early 20th-century architecture.
Riders can pick from a trove of destinations that include overlooks on the Blue Ridge Parkway to the west, 1,740-foot city panoramas from Mill Mountain to the south, and lakeside views in 12,700-acre Carvins Cove Natural Reserve to the east. Other highlights include a sporty BMX-style pump track in Wasena Park, a prograde cyclocross course in Fallon Park, and the 42-room, Georgian-revival-style Fishburn Mansion and Museum, which dates to 1907.
Get more info from Roanoke Parks & Rec: PlayRoanoke.com/Maps
Carvins Cove, east of Roanoke. Photo
by Molly Hagen | The City of Roanoke Parks and Recreation
Eat • Drink • Stay
Stay a block from the Roanoke River connector, Mill Mountain Greenway, in a purpose-built 1907 Georgian Revival firehouse. The Fire Station One Boutique Hotel has been lovingly renovated to retain original elements like pressed-tin ceilings and deep-well skylights. Its seven suite-style rooms are lavishly outfitted with subway-tiled bathrooms and midcentury-style furniture, lamps, and light fixtures. FireStationOne.com
Twin Creeks Brewpub awaits just off the Blue Ridge Parkway in a rustic but neatly overhauled 1790s tavern in 1,100-acre Explore Park. Take your pick from nine house brews or a fleet of Virginia wines and ciders. A menu of burgers, dogs, wings, and nachos rounds out the package. TwinCreeksBrewing.com/Brewpub
Show Pony in Roanoke’s Grandin Village is a bar-forward neighborhood joint, with comfort food in a refined setting. Opened last year by Chef Jeff Farmer and Cass Moser (from Stock Bistro), it serves refined yet accessible comfort food in a kitschy setting. ShowPonyGV
Charlottesville
Charlottesville lies nestled between the Blue Ridge and Southeast mountains, and is known as a melting pot for scenic beauty, cosmopolitan sophistication, and outdoors-friendly culture. Forward-thinking officials have helped showcase the former and fuel the latter by partnering with proactive bike clubs, businesses, state agencies, and conservation organizations to create an uncanny 36-mile network of dedicated greenways and nature trails.
Parks & Trails
When it comes to municipal hike and bike paths, the Rivanna Trail may well be Virginia’s crown jewel. The 20-mile route meanders through a string of six city parks and forested buffers on the banks of its eponymous river and various tributaries to enshrine Charlottesville in a 20-mile necklace of urban wilderness. That said, much of the route is single-track packed dirt, so riders will need an off-road-capable bike to enjoy it.
If dirt riding isn’t your thing, other options abound.
The John W. Warner Greenway, for instance, brings 3.5 miles of paved, mostly rail-to-trail riding that passes through expansive meadows, the Botanical Garden of the Piedmont, and 150-acre McIntire Park. The 2.1-mile Saunders-Monticello Trail, meanwhile, waits just outside of town and connects 89-acre Kemper Park to Jefferson’s historic estate and soaring, 1,000-foot views of the city.
Get more info from Charlottesville Parks & Rec: Charlottesville.gov/659/Trails
The annual Loop de Ville Trail Festival celebrates the 20-mile Rivanna Trail encircling Charlottesville. Photo by Cassidy Girvin | Piedmont Environmental Council
Eat • Drink • Stay
Kimpton The Forum Hotel sits beside the University of Virginia’s Darden School of Business within 500 feet of the Rivanna Trail. Expect modern, elegant rooms paired with Jeffersonian-style design features and rear grounds that open onto the oasis-like Tahija Arboretum & LaCross Botanical Gardens. ForumHotelCharlottesville.com
The Rivanna Trail passes within a stone’s throw of Högwaller Brewing. The brewpub overlooks the river and offers a rotating cast of house-made beers, regional wines, and spirits, plus a menu of tasty burgers and brats. HogwallerBrewing.com
Find Ivy Inn Restaurant a mile from the hotel in a lavishly overhauled 1816 home-turned-eatery that’s been family-owned since 1995. Chef Angelo Vangelopoulos’ seasonal menus change daily and showcase a French approach that also pays homage to his Greek heritage, longtime Southern residency, and love of Italian cuisine. IvyInnRestaurant.com
Lynchburg
An ongoing downtown renaissance has brought new life to Hill City, and greenway connectors to iconic parks and natural areas are part of the package. Signature rides include James River overlooks, historic railroad trestles, a restored 19th-century canal, Blue Ridge Mountain vistas, and some of the state’s best urban wildlife viewing.
Parks & Trails
Lynchburg’s top greenways are found adjacent to downtown in and around a pair of designated natural areas. The paved, 3-mile-long Blackwater Creek Trail begins at Linkhorne Middle School near the gorgeously landscaped Awareness Garden complex and pursues its namesake waterway east through 300 acres of dense riparian forests. Highlights include a couple of high wooden railroad trestle crossings, near omnipresent views of the creek, and an abandoned 500-foot-long stone railroad tunnel carved in 1850.
Pass beneath the Point of Honor Bridge into the lower downtown area and continue through the 8-acre Riverfront Park to the entrance of Percival’s Island Natural Area. Cross the James River via a 500-foot-long railroad trestle that brings stunning views of the city. A paved, two-lane trail runs the wooded, 1.5-mile length of the island and delivers riders to a second trestle crossing.
Get more info from Lynchburg Parks & Rec: LynchburgParksAndRec.com/Trails
Percival’s Island in the James
River in Lynchburg
Eat • Drink • Stay
The Virginian occupies an immaculately restored Beaux-Arts style downtown building that dates to 1913. Savor drinks at the rooftop bar and revel in historic vestiges like a first-floor lobby with barrel-vaulted, 30-foot ceilings, curved stained-glass skylights, and grand marble staircases. Spacious rooms and suites boast luxe modern accoutrements and incredible views of the river and city. TheVirginianHotel.com
Drop in for craft brews, ciders, or cocktails at Waterstone Pizza on the ground floor of the historic Craddock Terry Hotel. The wood-fired pizzeria and brewpub oozes ambience with exposed stone walls and massive, century-plus-old wood beams. It sits within a few hundred yards of Percival’s Island. WaterstonePizza.com; CraddockTerryHotel.com
Follow a pedal-packed day with dinner at the hip and intimate Dish Restaurant & Wine Bar. An extensive vino menu complements inspired seasonal small plates like seared scallops with a cranberry-apricot relish. DishDowntownOnMain
This article originally appeared in the October 2025 issue.
