Follow Your WanderLOVE: Virginia's Premier Outdoor Adventure Destinations

While wanderlust ignites a strong desire to travel, in Virginia we call it WanderLOVE. Captivating landscapes—from the majestic Blue Ridge Mountains to the pristine Eastern Shore—embody this passion. Experience it firsthand with our expert-curated itineraries to Virginia's top outdoor destinations, trusted by adventure enthusiasts statewide.

—RICHMOND—

The historic James River flows through Virginia's capital, earning its 'River City' moniker. Richmond features rare urban Class III and IV rapids, drawing adventurers for thrilling river experiences. Complement these with extensive mountain biking and hiking trails in the city and nearby Pocahontas State Park, boasting over 60 miles of paths from beginner to expert levels.

Trip Highlights:

• Kayaking trip down the James River with Riverside Outfitters
• Test your mountain biking skills at Pocahontas State Park, then kayak, canoe, paddleboard or fish on beautiful Swift Creek Lake
• Climbing lesson with Triangle Rock Club
• Bike to Upper Shirley Vineyards and back on the Virginia Capital Trail

Outfitters and Guides:

• Riverside Outfitters
• Triangle Rock Club (indoor rock climbing, yoga, and fitness classes including TRX)
• Peak Experiences (both indoor and outdoor climbing expeditions)
• PedegoRVA (electric bike rentals and tours of Hollywood Cemetery, Richmond neighborhoods, or a BBQ tour along the Virginia Capital Trail)
• Segway of Richmond
• Richmond Rides (themed bike tours of Richmond)
• Pocahontas State Park

See the Full Richmond Itineraries, Part 1 & Part 2

—SHENANDOAH VALLEY—

Discover Virginia's stunning Shenandoah Valley on a three-day escape featuring horseback riding, kayaking, and hiking amid the foothills of Shenandoah National Park and George Washington and Jefferson National Forests.

Trip Highlights:

• Horseback riding to Edith Gap for views overlooking the Shenandoah River with Fort Valley Ranch
• Kayaking down the scenic Shenandoah River
• Hiking at Big Schloss
• Test your fearlessness with Skydive Shenandoah
• Mountain bike through challenging terrain at Bryce Bike Park or Massanutten Mountain Bike Park
• Set out on a rock climbing adventure with Ridge Climbing & Rappelling Excursion
• Try the new sport of FlingGolf
• Traverse, climb, and soar through the trees on a Guided Canopy Tour

Outfitters and Guides:

• Fort Valley Ranch
• Shenandoah River Outfitters
• Bryce Bike Park
• Skydive Shenandoah
• Massanutten Resort
• Woodstone Meadows Stables
• Massanutten Adventures
• Massanutten Mountain Bike Park

See the Full Shenandoah Valley Itineraries, Part 1 & Part 2

—PRINCE WILLIAM COUNTY—

Just 30 miles from Washington, D.C., Prince William County offers abundant parks and forests along the Potomac River to Bull Run Mountain foothills—ideal for hiking, biking, and paddling.

Trip Highlights:

• Horseback riding at Manassas National Battlefield Park
• Kayaking & Stand-up Paddle boarding on the Occoquan River
• Fishing & Boating at Leesylvania State Park
• Biking, Hiking and Camping at Prince William Forest National Park
• Miles upon miles of natural hiking trails near historic sites, mountains, rivers, and forests

Outfitters and Guides:

• Penguin Paddling
• Rivershore Charters (pontoon boat cruises)
• Battlefield Park Polo (horseback rides through Manassas National Battlefield Park)
• Sail NOVA

See the Full Prince William County Itinerary

—VIRGINIA’S BLUE RIDGE—

Home to the Blue Ridge Parkway, Skyline Drive, and Appalachian Trail, Virginia's Blue Ridge shines with natural splendor and adventures. Recognized as the East Coast's first Silver-Level Ride Center by the International Mountain Bicycling Association, it's hailed as 'America’s East Coast Mountain Biking Capital.'

Trip Highlights:

• Scale rock outcroppings along the Blue Ridge Parkway
• Cast your line in one of the state’s only urban trout fisheries
• Try caving on the Adventure Tour at Grand Caverns
• Paddle the four-mile stretch of the South River that winds through downtown Waynesboro
• Tackle rugged mountain-bike paths in George Washington and Jefferson National Forests
• Mountain biking the trails at Carvins Cove with Roanoke Mountain Adventures
• Paddle the Upper James River with Twin River Outfitters
• Hike the Peaks of Otter trails

Outfitters and Guides:

• Roanoke Mountain Adventures
• Twin River Outfitters
• Rockfish Gap Outfitters
• South River Fly Shop
• Blue Ridge Mountain Guides
• Grand Caverns

See the Full Virginia’s Blue Ridge Itineraries, Part 1 & Part 2

—SOUTHERN VIRGINIA—

Southern Virginia's rural expanses—from Blue Ridge foothills in Martinsville & Henry County to Lake Gaston and Philpott Lake—offer paddling, fishing, hiking, camping, and family-friendly pursuits.

Trip Highlights:

• Camping, swimming, fishing and more at Philpott Lake
• Smith River paddling and/or fishing excursions
• Hiking the Richard P. Gravely, Jr. Nature Preserve
• Walking, biking, running the Dick & Willie Passage Rail Trail
• Hunting fairy stones, swimming, horseback riding and more at Fairy Stone State Park

Outfitters and Guides:

• Goose Point Campground Smith River Outfitters
• Richard P. Gravely, Jr. Nature Preserve
• Bike Barn
• Fairy Stone State Park

See the Full Southern Virginia Itinerary

—EASTERN SHORE—

Virginia's Eastern Shore spans over 78,000 acres of parks, refuges, and a U.S. National Seashore, hugging Atlantic and Chesapeake coastlines with five walkable waterfront towns boasting shops, galleries, museums, and eateries.

Trip Highlights:

• Kayak out to Holly Bluff, a private, off-the-grid Atlantic island with Burnham Guides. Paddle through a delicate wildlife refuge teeming with wildlife, tour a 1930’s hunting lodge and play on the private beach, Relax and picnic on a veranda overlooking the water.
• Boat out to Virginia’s wild barrier islands, the longest stretch of undeveloped outer banks remaining on America’s East Coast. Captain Meriwether Payne, of Seaside Ecotours, whose family has deep roots in the area, has extensive knowledge of marine life, shore birds and the history of these mystical islands.
• Kayak to a winery with SouthEast Expedition’s “Paddle Your Glass Off” Tour
• Get a bird’s eye view of the stunning Eastern Shore peninsula surrounded by water on three sides. You’ll be miles above the earth, gliding like a bird in flight, with Virginia Hang Gliding.
• Hike and paddle Kiptopeke State Park, a beachfront preserve, where you can kayak out to the concrete WWII “ghost ships” and hike miles of maritime forest with stunning views out over the Chesapeake Bay.
• Experience the wild barrier islands, Chesapeake Bay, and Chincoteague ponies and lighthouse by kayak, while staying in an historic lodging in the 1680 Colonial port of Onancock.
• Take a sunset boat cruise out of Cape Charles as the sun sets over the vast Chesapeake Bay horizon. You’ll meet up with the Cape Charles Boat Tour Company at the town harbor, just a few steps from the town’s bustling center.
• Learn to sail with Onancock Sailing Adventures

Outfitters and Guides:

• SouthEast Expeditions
• Seaside Ecotours
• Virginia Hang Gliding
• Kiptopeke State Park
• Burnham Guides
• Cape Charles Boat Tour Co.
• Onancock Sailing Adventures

See the Full Eastern Shore Itineraries, Part 1 & Part 2

—CHESAPEAKE—

Chesapeake's waterways brim with watersports, preserves, and parks. Explore Chesapeake Waterways' 22+ miles of premier kayaking, plus Northwest River Park's 763 acres of trails.

Trip Highlights:

• Kayaking the peaceful Dismal Swamp along the tall cypress trees, then hiking the Dismal Swamp Canal Trail
• Travel the Virginia Birding and Wildlife Trail for a closer look at Virginia’s coastal wildlife
• Hike, bike, paddle boats and canoe at Northwest River Park

Outfitters and Guides:

• Adventure Kayak Tours
• Northwest River Park

See the Full Chesapeake Itinerary

—FREDERICKSBURG—

Fredericksburg's outdoor offerings suit all skill levels along the Rappahannock River—Eastern America's longest free-flowing river—perfect for paddling, climbing, and fly fishing.

Trip Highlights:

• Stand-Up Paddle Boarding lesson on the tidal section of the Rappahannock River
• Boards, Boats and Brews Friday Night Paddle
• Rock Climbing along the banks of the Rappahannock River
• Fly Fishing the warm waters of the Rappahannock River

Outfitters and Guides:

• River Rock Outfitter
• Twin Junction Outfitters

See the Full Fredericksburg Itinerary

—ORANGE—

Orange region's breathtaking Central Virginia scenery shines at The Market at Grelen. Enjoy horseback riding, kayaking, and aerial views via their expert Outdoor Adventure itineraries, blending self-paced exploration with local delights.

Trip Highlights:

• Kayak the Rapidan River with Rapidan River Kayak Co.
• Riverside picnic lunch provided by The Market at Grelen’s Casual Cafe
• Tandem skydiving at Skydive Orange
• Hiking on Grelen’s five-mile trail system
• Picnic lunch and private sparkling Virginia wine flight at the top of the Overlook Trail
• Virginia beer flight tasting on The Market at Grelen’s stone terrace

Outfitters and Guides:

• The Market at Grelen
• Rapidan River Kayak Co.
• Skydive Orange

See the Full Orange Itinerary

—MIDDLE PENINSULA ON THE CHESAPEAKE BAY—

Gloucester and Mathews counties on Virginia's Middle Peninsula deliver kayaking, paddleboarding, and fishing charters along the Chesapeake Bay, paired with fresh seafood tastings.

Trip Highlights:

• Take a guided kayak trip and learn about the history of the indigenous peoples of Tidewater before colonists settled.
• Reel in a fresh catch on a Chesapeake Bay fishing charter. Get down to your roots and pick some fresh blue crabs at happy hour off of Tabbs Creek
• Take a Deadrise Boat Charter around the East River at sunset where you’ll shuck and eat a fresh raw oyster
• Kayak around the third oldest lighthouse on the Chesapeake Bay and enjoy the beach

Outfitters and Guides:

• Bay Country Kayaking
• Beaverdam Park
• Bay Fly Fishing
• Inn at Tabbs Creek and Chesapeake Paddling Company
• Mathews Deadrise Charters
• Mobjack Bay Kayaking

See the Full Middle Peninsula Chesapeake Bay Itinerary

—SOUTHWEST VIRGINIA—

Southwest Virginia's Blue Ridge haven, especially Abingdon, blends world-class hiking, biking, fishing, and bouldering with historic charm, arts, dining, and nightlife—accessible via local guides and shuttles.

Trip Highlights:

• Biking the Virginia Creeper Trail with Virginia Creeper Trail Bike Shop
• Meeting the wild ponies of Grayson Highlands State Park
• Paddling the North Fork of the Holston River with Adventure Mendota
• Guided hike to The Great Channels with Feeld Trips

Outfitters and Guides:

• The Virginia Creeper Trail Bike Shop
• Feeld Trips
• Adventure Mendota
• Virginia Creeper Fly Shop
• SunDog Outfitters

See the Full Southwest Virginia Itinerary