22 upcoming events in Oswestry
October 2026
Makers Market
Artisan makers market on Bailey Head, Oswestry, showcasing local craft producers, food stalls and handmade gifts.
Ribbons Tour, Hermon Chapel Arts Centre
Rebecca Nash, Sara Colman and Henrik Jensen bring their Ribbons Tour to the intimate converted Welsh chapel in Oswestry, a small 110-seat room that suits close-up jazz and folk-leaning music.
Practical Magic Halloween Paint & Sip, Crow & Compass
A witchy-themed evening of guided painting with a drink in hand at Crow & Compass Art Studio in Oswestry, a relaxed creative night out in the run-up to Halloween.
Moon & Magic Market
Handmade crafts and mystical-themed market at Oswestry Memorial Hall.
Oswestry Halloween Market
Halloween-themed market on Bailey Head in Oswestry town centre with spooky stalls, costumes and family activities.
November 2026
Oswestry Fireworks in the Park
Charity fireworks display with low-noise fireworks, laser light show and live music at Cae Glas Park, run with Oswestry Borderland Rotary.
Lost & Found: A Live Theatre Game, Oswestry Memorial Hall
An interactive live theatre game staged at Oswestry Memorial Hall where the audience takes part in the story, offering a playful afternoon of entertainment.
Remembrance Day Service and Parade
Oswestry's annual Remembrance Sunday commemorative service and parade through the town.
Oswestry Folk: Harp & a Monkey
Live folk music night at Oswestry Cricket Club.
Oswestry Cricket Club Comedy Night #6
The sixth stand-up comedy night hosted by Oswestry Cricket Club on Morda Road, a lively local evening of live laughs in a community setting.
Oswestry Christmas Lights Switch On
Official start of Christmas in Oswestry town centre, with the switching on of the festive lights and entertainment.
Santa Steam Train - Cambrian Heritage Railway
A magical Santa adventure combining Christmas experiences with heritage steam trains at Cambrian Heritage Railway, Oswestry Station. Runs weekends. Does not operate to Weston Wharf. Booking essential.
December 2026
An Evening with Lisa Jewell: It Could Have Been Her, Oswestry School
Bestselling thriller author Lisa Jewell talks about her novel It Could Have Been Her at Oswestry School. Tickets were showing as almost full, so book early if interested.
Christmas Live
Bringing all the fun of the fair to Oswestry town centre for one night only, part of the town's Christmas festivities.
Oswestry Christmas Live
Fairground rides and festive entertainment fill Oswestry town centre for one night of Christmas celebrations.
Oswestry Christmas Parade
Festive parade through Oswestry town centre marking the countdown to Christmas, with floats and community groups.
Shropshire Santa 5K Run
A festive fun run through Oswestry suitable for all runners, part of the town's Christmas events programme.
Oswestry Illuminated Tractor Run
A charity event featuring a procession of illuminated tractors through Oswestry, raising funds for local causes.
Oswestry Christmas Artisan & Late Night Market
Late-night artisan market on Bailey Head with Christmas gifts, crafts, festive food producers and live music.
Christmas Artisan & Late Night Market
An extra-special late night artisan market in Oswestry town centre with Christmas gifts, crafts, festive food and drink producers, and live music.
Mince Pie Specials - Cambrian Heritage Railway
Festive heritage train journeys through the Shropshire countryside aboard vintage carriages, with mince pies included.