Banff, Alberta, Canada
Nearly 120 miles of mountain-bike trails wind through Banff National Park, where the high-alpine scenery–striated peaks, aquamarine lakes, and glaciers–is among the world’s most stunning. In fact, the town itself is in the park. Rent wheels at Bactrax or The Bike Stop, then warm up on the paved Banff Legacy Trail. After a night at the boutique Juniper Hotel, which offers on-site bike tuning and rentals, fuel up on whole-wheat flaxseed waffles at Wild Flour Bakery, then tackle the Icefields Parkway: The scenic road follows the Bow River all the way to Lake Louise and Jasper, with steady climbs to 7,000 feet and long, sweeping descents.

Burlington, Vermont
Choose from among dozens of rides mapped by the Green Mountain Bicycle Club: a tour of covered bridges, a Cabot cheese tasting, or a loop through the quad-torching Greens. Recover overnight at the historic Willard Street Inn, a Queen Anne–style mansion with a marble-floor solarium and a bike rack near the front door. Nearby, hop on the Burlington Bike Path (a paved 7.6-mile route) and stop by the Skinny Pancake for crepes topped with Vermont butter and maple syrup. From there the pathway connects to 1,300 miles of the Lake Champlain Bikeways system, a network of routes that rolls through classic New England scenery all the way to Quebec.

Charleston, South Carolina
The city is known for graceful antebellum houses and Southern manners, but Charleston’s cycling culture is surprisingly rich. Real estate agents show properties by bike. The popular Taco Boy features dedicated bike racks out front. The elegant Planters Inn hosts cycling tours and the Vendue Inn lends out beach cruisers. Local club Coastal Cyclists leads daily rides that show off both the old and new South, taking in barrier islands, plantations, and greenways.

Healdsburg, California
This quaint town is an ideal staging ground for exploring Sonoma wine country by bike. Start rides with a homemade energy bar at the Jimtown Store and end with gelato sandwiches at Bovolo. Book a tasting ride with Wine Country Bikes, or visit on August 21 for the Tour de Vine, during which you’ll ride with local vintners and chefs and feast on goat cheese and baguettes at the farmers’ market. Sleep off your food coma at the new eco-chic h2hotel, which offers earth-friendly amenities along with secure bicycle storage and a collection of hip Public bikes guests can take for a spin.

Ketchum, Idaho
With 400 miles of trails crossing the surrounding Sawtooths, the laid-back resort of Ketchum/Sun Valley is a legit, never-ride-the-same-singletrack-twice destination. In town, bike culture is vibrant: A half-dozen shops rent out wheels and former world champions scarfthin-crust pizza and microbrews at Wiseguy. Turn in any direction and you’ll find either a ski lodge–the Sun Valley Lodge and the Best Western Tyrolean offer bike storage–or a $9K carbon beauty leaning against a deck.

Traverse City, Michigan
Visit this northern Michigan city in August for the Cherry-Roubaix (with Euro-style cobbles), the Third Coast Bicycle Festival, and DALMAC, a huge multiday ride that passes through the area. Stay at the Traverse Bay Inn, which has a fleet of bikes for guests and sits on the 10.5-mile Traverse Area Recreational Trail (TART). Spin past Grand Traverse Pie and sample a cherry-crumb slice, then continue to the 18-mile-long Old Mission Peninsula for orchards, historic homes, and panoramic views. Want to climb faster? Brick Wheels, also on TART, rents out high-end road bikes.