January is one of South Oxfordshire’s best-kept secrets. The festive rush has faded, the countryside is calm, and the pace of life slows to something altogether more restorative. Frost settles over rolling hills, riverside paths feel wonderfully empty, and village pubs glow with warmth after a crisp winter walk.

For travellers who enjoy quiet beauty, cultural moments, and the feeling of discovering a place at its most authentic, January is an ideal time to visit. From heritage events and winter markets to guided walks and live performances, South Oxfordshire still has plenty happening—just without the crowds.

Here’s what’s on across the region in January 2026, and why this is the perfect time to explore the Thames Valley and Chiltern foothills.

Winter Highlights Across South Oxfordshire

Guided Winter Walks in the Chilterns

Dates: Saturdays, 10–31 January 2026
Locations: Watlington Hill, Nettlebed Woods, and the Thames Path between Goring & Streatley

Local walking groups and countryside trusts host guided winter walks throughout January, taking in sweeping valley views, ancient woodland, and historic market towns.

Why you should attend:
Winter reveals the landscape in a different way. Bare trees open up long-distance views, wildlife is easier to spot, and the air feels sharper and clearer. These walks often include local history, folklore, and nature insights you won’t find on a map.

What’s unique about it:
South Oxfordshire’s blend of riverside paths and rolling chalk hills makes each walk feel varied. You might start beside the Thames in Goring and finish on Watlington Hill with panoramic views across Oxfordshire—something few regions can offer in a single morning.

Henley-on-Thames Winter Artisan Market

Date: Saturday 17 January 2026
Location: Market Place, Henley-on-Thames

A scaled-down, seasonal version of Henley’s famous markets, this winter edition focuses on local makers, food producers, and craftspeople.

Why you should attend:
It’s relaxed, friendly, and easy to explore. You can chat with stallholders, sample local produce, and pick up handmade gifts without the bustle of peak-season crowds.

What’s unique about it:
Set against Henley’s historic riverside streets, the market blends heritage with creativity. It’s a snapshot of local life—authentic, community-led, and quietly charming.

Wallingford Winter Weekend

Dates: 23–25 January 2026
Location: Wallingford Town Centre & Castle Meadows

This town-wide winter weekend combines pop-up stalls, heritage talks, and family-friendly activities celebrating Wallingford’s Roman and medieval roots.

Why you should attend:
It’s an easy way to experience the town’s history, independent shops, and riverside setting all in one visit.

What’s unique about it:
Wallingford’s preserved medieval street plan and castle ruins create an atmospheric backdrop. In winter, with fewer visitors, the town feels like it belongs to you.

Theatre & Live Performance Evenings

Dates: Throughout January 2026
Locations: Corn Exchange (Wallingford), Kenton Theatre (Henley), village halls in Benson, Chalgrove & Dorchester

From small-scale drama and comedy nights to acoustic music and literary talks, January’s programme is packed with intimate performances.

Why you should attend:
These venues offer high-quality entertainment in welcoming, local settings. Winter evenings are perfect for culture followed by a drink in a nearby pub.

What’s unique about it:
You’re not in a faceless auditorium—you’re in a historic town or countryside village. Performers are often just metres away, making the experience personal and memorable.

Quiet Season Heritage Visits

Dates: Daily throughout January 2026
Locations: Dorchester Abbey, Wallingford Museum, riverside heritage trails in Goring & Benson

Many heritage sites remain open in January, often hosting winter talks or self-guided themed trails.

Why you should attend:
With fewer visitors, you can explore at your own pace, ask questions, and enjoy uninterrupted views.

What’s unique about it:
South Oxfordshire’s history is woven into everyday life—from Roman roads to medieval market towns and literary landmarks. Winter visits feel reflective rather than rushed.

Why January Is the Best Time to Visit

• Walking trails without summer crowds

• Better value on accommodation

• Calm towns and villages

• Atmospheric winter landscapes

• A slower, more authentic pace of life

January in South Oxfordshire isn’t about ticking off tourist sights—it’s about feeling the place.

Stay with Pass the Keys

Whether you’re planning a countryside retreat near Watlington, a cultural weekend in Henley, or a riverside escape in Wallingford, Pass the Keys offers professionally managed holiday homes across South Oxfordshire. Each stay combines the comfort of a private home with hotel-level reliability—ideal for winter breaks when warmth, ease, and quality matter most.

After a day of frosty walks, heritage exploring, or live performances, return to a space that feels entirely your own. With Pass the Keys, January 2026 becomes more than a getaway—it becomes a true winter escape.