Cotswolds Bike Tour

Meet your guides in the charming university town of Oxford. Our journey begins with a brief transfer to the 800-square-mile area in the South of England that comprises the Cotswolds: spanning from Gloucestershire to Oxfordshire counties, the Cotswolds were designated an Area of Outstanding Natural Beauty (AONB) in 1966. It’s easy to see why, with peaceful stands of beech trees and limestone bedrock forming a grassland habitat unlike elsewhere in the UK. After a welcome lunch, kick things off with our first short ride through the ancient market town of Wotton-under-Edge. Continue spinning to the National Arboretum at Westonbirt, a wooded parkland with an English café where we’ll stop for the essential “cuppa” and cake. Then, check in at our home for the next two nights—a traditional country house and spa in Gloucestershire. Settle in by the fireplace before a cozy dinner at the hotel’s brasserie.

Meals: Lunch / Dinner
Destinations: Oxford, Wotton-under-Edge, Westonbirt
Accomplished: 23 miles / 37 km, elevation gain: 1,543 feet / 470 meters
Accommodations: Calcot & Spa

Today’s countryside loop follows quiet roads completely surrounded by the green expanse that’s so unique to the Cotswolds. Our first stop is Tetbury, a hilly market town where we’ll pause for coffee and a bit of a browse at the Highgrove shop, which retails sweet souvenirs and favorite products of His Majesty King Charles III. Then, ride north, covering miles of rolling countryside and passing the impressive Miserden Estate. Arrive in the peaceful village of Painswick for lunch, then pedal the rest of the way back to our hotel. Take the opportunity to stroll the gorgeous grounds or book a massage at the world-class spa before we transfer to the Woodchester Valley Vineyard. Taste a few well-earned glasses after a private tour at this boutique winery, which grows a selection of English varietals in a picturesque limestone valley. This evening, dine on your own at the hotel or in one of Tetbury’s many pubs.

Meals: Breakfast / Lunch
Destinations: Tetbury, Miserden, Painswick, Stroud
Accomplished: 41 miles/ 66 km; elevation gain: 2,700 feet / 821 meters
Accommodations: Calcot & Spa

The most iconic trait of the Cotswolds is its beautiful villages and towns built of pale-yellow Cotswold limestone—and today we plan to see as many as we can! Together known as The Slaughters, Upper and Lower Slaughter are heart-achingly picturesque and prime examples of quintessential Cotswold villages. Here, golden stone cottages are reflected in the meandering River Coln and bathed in beautiful light, treating us to some truly idyllic morning scenery. At lunchtime, pop into a traditional pub and sample some of the local lagers. Afterward, we’ll approach Bourton-on-the-Water, often called the Venice of the Cotswolds for the lovely footbridges that span the gentle River Windrush. There will be time to meander this pretty town and browse its boutiques before we check in to our hotel.

Meals: Breakfast / Lunch / Dinner
Destinations: Stow-on-the-Wold, Upper and Lower Slaughter, Bourton-on-the-Water
Accomplished: 42 miles / 67 km, elevation gain: 1,920 feet / 585 meters
Accommodations: Lords of the Manor Hotel

Begin riding right from our hotel through an undulating landscape to Chedworth Roman Villa, a ruin of unusual grandeur dating back to the second century. After exploring the site, we’ll return to the rolling hills and follow them towards stately Sudeley Castle, just outside the lovely village of Winchcombe. Take a deep dive into the dramatic 1,000-year history of this estate, once home to Queen Katherine Parr—the last (and surviving) wife of King Henry VIII who lies in rest on castle grounds. Our route completes itself at the attractive village of Broadway—so picture-perfect that it’s widely known as the “Jewel of the Cotswolds.” Dine on your own for lunch and take the afternoon to explore this adorable town off the bike, perhaps sampling a locally distilled Cotswold gin or whisky before a short transfer returns us to our charming hotel. Tonight, we’re treated to the tasting menu at our hotel’s own Atrium restaurant, perhaps the most sophisticated example of fine dining in the Cotswolds.

Meals: Breakfast / Dinner
Destinations: Chedworth, Winchcombe, Broadway
Accomplished: 35 miles / 57 km, elevation gain: 2,880 feet / 875 meters
Accommodations: Lords of the Manor Hotel

Our last day also happens to be one of the most memorable: set out towards Burford and cycle past breezy fields, herds of cows, and grazing sheep as we once again follow the River Windrush. Heading north, we ride through Wychwood Forest before meandering beside the River Evenlode. Savor the tranquility of rural England and lean into your riding rhythm before we hit a final stretch through the countryside and villages. Our destination is the very special Wild Rabbit restaurant, where the chef uses organic ingredients from the inn’s cottage garden to prepare our lunch. Our meal is a work of art starring locally raised game, edible flowers, and seasonal vegetables harvested that very morning—the perfect high note on which to end our week together. After lunch, your driver will transfer you back to Oxford.

Meals: Breakfast / Lunch
Destinations: Windrush, Oxford
Accomplished: 27 miles / 44 km, elevation gain: 1,400 feet / 418 meters