Fourteen named annual events in and around Henley. The big ones — Regatta, Festival, Rewind, the Literary Festival, the Living Advent Calendar — book up months ahead. Dates confirmed where possible from official sources, May 2026.
Two weeks of the calendar that define the town. The Royal Regatta sets up its mile-and-a-half course along the Thames; the Henley Festival follows it with five black-tie evenings on the same site. Book early. Our T&Cs apply stricter cancellation terms to bookings that include any Regatta night.
The defining event of Henley's calendar — six days of international rowing, picnic hampers, blazers, Pimm's, and the world's most photogenic stretch of river. Racing runs morning till evening; Sunday finals finish by 16:30. Free public viewing from the towpaths; ticketed enclosures (Stewards', Regatta, Fawley Bar) need advance booking and enforce strict dress codes.
hrr.co.uk ↗Black-tie nights of music, comedy and food on a floating stage on the Thames. 2026 headliners include Boy George & Culture Club, Sugababes, Lulu, Ezra Collective, Ronnie Scott's Jazz Orchestra with Laura Mvula, and Jo Whiley's 90s Anthems. Same site as the Regatta enclosures, repurposed.
henley-festival.co.uk ↗Trail race through the Chiltern woodland on the estate that's hosted half a dozen Hollywood films. Half marathon, 10K and 5K options through ancient woodlands and farmland. Muddy, scenic, properly tough.
For 5–16 year olds, with a team relay option. The warm-up to the main event the next day.
17th year. Sprint: 400m heated indoor pool swim + 25km countryside cycle + 5km flat grass run. Super Sprint: 200m / 12.5km / 2.5km — a good entry point for first-timers. Solo and team relay options.
The UK's premier women's-only regatta, running for over thirty years. Same iconic course as the Royal Regatta, much more relaxed atmosphere, free to watch from the towpath. Three new women's events added to the 2026 programme.
The only day of the year you can legally swim the 2.1km Royal Regatta course. ~400 swimmers enter the water at first light heading upstream from Temple Island. A bucket-list event for open-water swimmers, returning in 2026 under new organisers — register interest via the Henley Swim site.
See the headline block above. The defining week of Henley's year — racing runs morning till evening with Sunday finals by 16:30. Central Henley operates at peak energy throughout.
Black-tie music, comedy and food on a floating stage on the Thames. 2026 lineup includes Boy George & Culture Club, Sugababes, Lulu, Ezra Collective, Ronnie Scott's Jazz Orchestra with Laura Mvula, and Jo Whiley's 90s Anthems. Five evenings, food village, fireworks.
Two more open-water swim events from the team behind the Henley Classic — Club to Pub is a community-friendly 1.4km with a riverside pub at the finish; Thames Marathon is the brutal 14km downstream swim from Henley to Marlow.
The town's own one-day regatta — far less formal than the Royal, open to local clubs, schools and community crews. Family atmosphere, free to watch.
Three days of 80s and 90s nostalgia. Saturday headliner: The Human League. Sunday closer: The Proclaimers. Also on the bill: Tony Hadley, Kim Wilde, Roland Gift (Fine Young Cannibals), Soul II Soul, The Undertones, Nik Kershaw, Toyah, Peter Andre, Toploader, Louise, The Beat, Trevor Horn Band, Dodgy and Dave Hill's Slade. Inflatable Church (for Rewind weddings), Silent Disco, Pink Flamingo and River Stages. Sunday closes with fireworks.
One-day agricultural show held by the Henley & District Agricultural Association since 1891. Livestock classes, farming demos, ring events, food and craft stalls. Free shuttle bus from Boots in Henley and Platts in Marlow. The proper countryside version of Henley.
Ten days of author talks, panels and book signings. Nigella Lawson opens the festival; Julia Donaldson closes it. Schools programme runs alongside. Format combines in-person events in Henley and online streams.
Scenic half marathon crossing Henley Bridge and following the Thames valley. 10K, 5K and family fun run options run alongside; half marathon, 10K and 5K all start at 09:30.
The annual Christmas tree lights switch-on at 7pm, hosted by the Mayor of Henley alongside a VIP celebrity guest, the Christmas Card design winner, and Kenton Theatre pantomime characters. Carol singing, late-night shopping, market stalls.
Inspired by a Stockholm tradition — every evening in December a different "window" opens somewhere in town for a 20-minute live performance (carols, poetry, music, dance), each night raising money for a different local charity. One of the first of its kind in the UK, running since 2011.
Late June to mid-July. The busiest period of the year for our properties. Book 6+ months ahead. Our T&Cs apply stricter cancellation terms to bookings that include any Regatta night.
Late August. The next-busiest peak, particularly for groups.
Early October. Becoming a meaningful second peak in the year — worth booking ahead.
December is lovely for short breaks — central Henley is quiet by day, but the evenings have proper atmosphere.
If you're flexible on dates and want to dodge the crowds, mid-September and mid-May are arguably the prettiest weeks of the year — full summer foliage, low visitor numbers, restaurants without the wait.