We’ve rounded up the best events taking place this month to ensure you kick off 2020 with a great start!

Sports events in Cheltenham January 2020

There are plenty of sporting fixtures taking place this month including…

Horse and jockey at Cheltenham races

New Year’s Day Races

Date:  Wednesday 1 January

Location: Cheltenham Racecourse, Evesham Rd, Cheltenham GL50 4SH

Known as the Cheltenham Big Day Out.  This is a guaranteed way to start 2020 in style! New Year's Day hosts seven quality races, including two Grade 2s with trainers, jockeys and racegoers all hoping to get their year off to a flying start.

Under 18’s go free and the racecourse hosts complimentary family entertainment plus live music in The Centaur (Club/Tatts enclosure.

Full event details

Spectators looking through binoculars at Cheltenham RacesFestival Trials Day

Date: 25 January

Location: Cheltenham Racecourse, Evesham Rd, Cheltenham GL50 4SH

If you can’t make it on New Year’s Day, then there’s a second chance at racing this month with the Festival Trials Day.  Broadcast live on ITV Racing, it's the last Cheltenham raceday before The Festival and there is always an excitable atmosphere. Huge crowds gather to catch a glimpse of Festival contenders as they show the world what they're really made of. 

The racing highlight of Festival Trials Day is the Trial Cotswold Steeple Chase, often considered a trial for the Gold Cup in March. 

Full event details

A spectator using binocular

Cocklebarrow Races

Date: 26 January

Location: Near Northleach, Cheltenham, Gloucestershire, GL54 3PP

Seven competitive steeplechases offer the chance to kick off the January blues.  Enjoy the sport from a heated picnic tent with bar, which offers easy access to the paddock and bookmakers.  Highlights are a tough farmer competition, terrier racing, massive shopping hall, free kids zone including bouncy castle and rodeo. All day fun is guaranteed at this Point-to-Point, with plenty of activity for all age groups.

Full event details

Cheltenahm Town football players

Cheltenham Town FC Matches

Location:  Whaddon Road.  Postcode for SatNav: GL52 5NA 

There are possibly three home games at Jonny-Rocks Stadium this January (depending on if Northampton win their FA Cup tie on 4th January).  Confirmed matches to date are - 4 January verses Oldham Athletic and 11 January against Walsall.  Wrap up warm and go and support our local club!

Cheltenham Racecourse at winter with frost on the ground

Local winter walks

Of course you don't need to attend a local sports event to enjoy the great outdoors and blow away a few cobwebs.  We've rounded up eight of our favourite local walks which are the perfect antidote to festive over-indulgence... Best Cheltenham Walks

Unmissable family events this January in Cheltenham…

Rubber Duck in a stream

Annual Rubber Duck Race

Date: Sunday 13 January 2019 11am – 1pm

Location: The Boating Lake, Pittville Park, Evesham Road, Cheltenham, Gloucestershire, GL52 3AB

Head on down to Pittville Park this year to celebrate National Rubber Duck Day! Sponsor a duck in the rubber duck races or try your hand at hooking a duck for a chance to win a prize.  Food and drink will be on sale.  There’s something for the whole family to do and money raised goes to Sue Ryder Leckhampton Court Hospice.

Full event details

December may be over but it’s not too late to enjoy panto in Cheltenham…

Performers taking a bow - Cinderella Everyman


Dates: 2-5 & 7-12 January

Location: Everyman Theatre, 7-10 Regent Street, Cheltenham, Gloucestershire, GL50 1HQ

Polish your pumpkins, dust off your gowns and grab your glass slippers to join a host of crazy characters at the Everyman Theatre.  Tickets for the last few performances of this popular panto are limited so you’ll have to be quick to book. 

Check out our review of Cinderella at the Everyman Theatre.

Poster for Robinson Crusoe performance

Robinson Crusoe and the Pirates

Dates: 16 – 19 January

Location: Bacon Theatre, Dean Close School, Shelburne Road, Cheltenham, Gloucestershire, GL51 6HE

This amateur dramatic performance of Robinson Crusoe is guaranteed to cheer up your January.  There will be lots of audience participation, a hilarious Dame, colourful costumes and lots of laughs.

Full details here.

Actors from Wind in the Willows looking over a river dressed in costume

The Wind in the Willows

Dates: 24 – 25 January

Location: Irving Studio, Everyman Theatre, 7-10 Regent Street, Cheltenham, Gloucestershire, GL50 1HQ

Follow the adventures of handsome Ratty, innocent Mole, wise Badger and of course the incomparable Toad as they row, ride and run on and around the banks of The River in an escapade suitable for the whole family!

An unmissable January event for shoppers! 

Cheltenham Boutique Sale poster

Cheltenham’s Boutique Sale

Date: Sunday 27 January from 11am – 3pm

Location: Princess Hall, Cheltenham Ladies College, Bayshill Rd, Cheltenham, Gloucestershire, GL50 3EP

Shop until you drop at Cheltenham's Boutique Sale. Shoppers will be able to benefit from discounts of up to 70 per cent from some of the Cotswolds' favourite retailers. The popular event, organised by Cheltenham BID, will be held for the fourth consecutive year in the beautiful surroundings of Princess Hall at Cheltenham Ladies College. Entrance is free.

Full Event Details

Enjoy afternoon tea in Cheltenham this January

Afternoon tea has always been a popular past time in Cheltenham.  Many venues are offering themed afternoon teas or brunch this month which is a splendid way to escape from the cold and enjoy quality time with family/friends! Here are a few of our favourites…

Afternoon Tea selection including cakes and sandwiches at Cafe Rouge

Chocolate Afternoon Tea at Café Rouge

Dates: 6 January – 29 February.

Location: Café Rouge, 31 - 41 The Promenade, Cheltenham, Gloucestershire, GL50 1NW

Indulge in plenty of chocolate treats, including chocolate fondue, chocolate cakes and their brand new chocolate s'mores croque with a decadent chocolate & marshmallow filling. Just 29.95 for two to share, exclusively available from 6th January - 29th February 2020.

Full details here.

Vegan Afternoon Tea

Dates: 6 – 31 January Location: Café Rouge, 31 - 41 The Promenade, Cheltenham, Gloucestershire, GL50 1NW This tasty treat is the ultimate gift for vegans and non-dairy diets or the perfect way to get involved in Veganuary 2020! You'll enjoy tasty baguette bites and olives, classic scones and a sweet selection of plantisseries; all for just 29.95 for two to share.

Full details here.

The Ivy -n Cinderella themed cocktail

Meet the stars of Cinderella over brunch at The Ivy Montpellier Brasserie

Date: 5 January

Location: The Ivy Montpellier Brasserie, Rotunda Terrace, 3 Montpellier St, Cheltenham, Gloucestershire, GL50 1SD

The perfect family day out.  Enjoy brunch at the brasserie from 10am before heading to The Everyman Theatre to watch a matinée performance of their popular Cinderella pantomime at noon. Available for the whole family, diners can choose from a selection of brunch classics as well as a choice of two bespoke Cinderella-inspired cocktails, including a non-alcoholic version for all ages to enjoy.

Full details here.

Afternoon Tea at No131 Promenade including eclair and macaroons

Afternoon Tea at No.131

Dates: Daily 3pm – 5pm

Location: No.131, 131 The Promenade, Cheltenham, Gloucestershire, GL50 1NW

Enjoy sweet and savoury treats whilst sinking into one of No 131's sleek velvet sofas or find a shady spot on the Mediterranean inspired outdoor terrace.

Full details here

Live performances this January in Cheltenham

We are spoilt for choice this month with live music and theatre productions.  Here are a selection of the best performances.  Check out our What's On in Cheltenham Guide for further inspiration.

Musician from Bournemouth Symphony Orchestra

Bournemouth Symphony Orchestra New Year Strauss Gala

Date: 4 January

Location: Cheltenham Town Hall, Imperial Square, Cheltenham, Gloucestershire, GL50 1QA

Fast becoming an annual favourite, the New Year Strauss Gala returns once more to celebrate the arrival of 2020 with an uplifting selection of waltzes, marches and arias by the Waltz King and his contemporaries.

Full details here.

A Country Night in Nashville

Date: 10 January

Location: Cheltenham Town Hall, Imperial Square, Cheltenham, Gloucestershire, GL50 1QA

This show recreates the scene of a buzzing Honky Tonk in downtown Nashville, perfectly capturing the energy and atmosphere of an evening in the home of country music. Prepare to be transported on a musical journey through the history of Country, featuring songs from its biggest stars both past and present.

Full details here.

Thank You For The Music

Date: 16 January

Location: Everyman Theatre, 7-10 Regent Street, Cheltenham, Gloucestershire, GL50 1HQ

This international smash-hit tribute show brings all of ABBA's number one hits to the stage in a production like no other. The hugely popular show, combines the unmistakable harmonies, colourful costumes, and dazzling performances by an all-star cast that'll have you thanking ABBA for the music again and again!

Gladys Knight: Midnight Train to Georgia

Date: 17 January

Location: Everyman Theatre, 7-10 Regent Street, Cheltenham, Gloucestershire, GL50 1HQ

Capturing the essence of the multi award winning Ms Gladys Knight, Hayley Ria Christian portrays her, and truly brings the magic that Gladys Knight provides on stage. Featuring the hit songs like Baby Don't Change Your Mind, Help Me Make it Through the Night, Try to Remember/The Way We Were, Part Time Love, Licence To Kill and her signature tune Midnight Train To Georgia.

Full details here.

Elkie Brooks

Date: 18 January

Location: Cheltenham Town Hall, Town Hall, Imperial Square, Cheltenham, Gloucestershire, GL50 1QA

With numerous hit singles, a million selling albums and awards, Elkie Brooks’ annual tours are a treat for fans old and new.  Elkie will perform some of her classic hits, blues and jazz.

Full details here.

Wedding Shows in Cheltenham this January

January is the month for Wedding Shows with not one but three taking place in town!

Wedding couple in front of Pittville Pump Room

The Cheltenham Wedding Expo

Date:  Sunday 19 January 11am -3pm

Location: Pittville Pump Room, Pittville Park, Cheltenham, Gloucestershire, GL52 3JE

If you got engaged over the festive season then it’s time to start planning! The Pump Rooms in Pittville Park is the place to be this January. Surrounded by beautiful parkland, in the unique Grade I listed venue, meet some of the area’s finest wedding professionals and experts, and get planning your dream wedding!

Full event details

Cotswold Wedding Fayre

Date: 18 & 19 January 11am – 4.30pm Sat & 11am – 4pm Sun

Location: Glenfall House, Mill Lane, Charlton Kings, Cheltenham, Gloucestershire, GL54 4EP

Enjoy the cosiness of Glenfall at winter over a glass of mulled cider and a mini mince pie by the roaring fire as you soak in all the inspiration you need for your big day.

This is the biggest Cotswold Wedding Fayre throughout the year which means - more award-winning suppliers, more inspiration and bigger and better wedding fayre special offers!

Full event details

Wedding Fayre at Hatherley Manor

Date: 29 January 6pm – 8pm

Location: Hatherley Manor Hotel & Spa, Down Hatherley Lane, Down Hatherley, Gloucester, Gloucestershire, GL2 9QA

View the beautiful suites all laid out for a Wedding Breakfast while walking around with a glass of bubbles. You will also get the chance to meet experienced suppliers who will be able to help you with all your ideas to make your wedding day extra special.

Full event details

Planning ahead for 2020 in Cheltenham

Cheltenham’s beautiful landmark buildings will be dramatically lit up to the delight of visitors in February 2020 as the spectacular Light Up Cheltenham returns for a third year.

Starting on the 1 February and finishing on 23 February, over 30 buildings and landmarks will be bathed in light with the stunning backdrop of the most complete Regency town in the UK.

Find out everything you need to know, including when you can see Spark the popular glow band from last year and times/prices of the observation wheel here – Light Up Cheltenham 2020.

Planning a short break in Cheltenham for 2020? 

We have a fantastic range of accommodation to suit any style, taste and price range. Mixing luxury and budget, boutique and traditional, we know you’ll find the perfect place to lay your head or indulge and relax. Click here to research and book your Cheltenham Hotel and here to check out all of our incredible Cheltenham Restaurants and Bars, many of which are award winning. 


New Year's Day Racing - Abandoned
Horse Racing
New Year's Day Racing at Cheltenham Racecourse

Sadly, the New Year's Day racing at Cheltenham has been adandoned. Following 85mm of rainfall on the racecourse since last Wednesday, there are areas of waterlogged ground across the width of the course and it is therefore not raceable. Having entered Tier 3 on 26 December, Cheltenham Racecourse was already unable to welcome spectators, although racing was due to go ahead behind closed doors.


The Everyman's annual, family-friendly pantomime is back! Cinderella features the hilarious return of Tweedy as Buttons, Cinderella's best friend in this rags to riches tale.

Cheltenham Town vs Oldham Athletic
Cheltenham Town vs Oldham Athletic

CTFC vs Oldham Athletic, SkyBet League Two

The Ivy Montpellier Brasserie serves up Alice in Wonderland Afternoon Tea
Food and Drink
The Ivy Montpellier Brasserie serves up Alice in Wonderland Afternoon Tea

From Monday, 5 August, The Ivy Montpellier Brasserie will be serving up a special Alice in Wonderland-themed Afternoon Tea in celebration of Cheltenham being the location in which Lewis Carroll was believed to have met the original Alice.



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