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8 events in the Cotswolds this autumn and winter (and what to wear to them)

PUBLISHED: 15:48 16 September 2016

Lower Slaughter in the autumn © KN, Shutterstock

Lower Slaughter in the autumn © KN, Shutterstock


The colder months may be on the way, but that’s no reason to hide away indoors. Here are the autumn and winter highlights in the Cotswolds calendar to warm you up, plus special suggestions from Olivia May womenswear boutique in Oxford to make sure you’re looking your best

1. The Autumn Classic, Prescott Speed Hill Climb

1-2 October

The roaring of muscle cars, the growling of revving engines and the swinging sounds of early Rock n’ Roll will all ring out from Prescott Speed Hill Climb as the Autumn Classic returns for its seventh year. Over a weekend of car displays and championship races on the 1000-metre course, plus some all-American entertainment, the event celebrates the best American cars from this side of the Atlantic. From Cadillacs to Chevvys, Model Ts to Mustangs and Stanley Steemers to Hotrods, the popular Autumn Classic is a treat for the motoring enthusiast.

What to wear

The unpredictable weather in England means no outdoor event in the autumn is complete without something warm to wear. If you’re not going the full authentic look, this cosy body warmer from Rundholz Black Label is stylish and practical with an asymmetric zip and snap fastening. Team it with a long sleeved jersey top, jeans and a pair of boots to finish the look. Click here to get the full outfit.

Outfit put together by Olivia May for the Autumn Classic, Prescott Hill ClimbOutfit put together by Olivia May for the Autumn Classic, Prescott Hill Climb

2. Cheltenham Literature Festival

7 – 16 October

Book lovers will, once again, flock to Cheltenham for the UK’s leading festival of literature. The spa town hosts more than 600 of the most prominent writers, poets, comedians, politicians and actors (to name a few), who will be giving talks, interviews and workshops all about the written and spoken word. Chefs will also be ready, knives or whisks in hand, to give scrummy cooking demonstrations.

This year’s 10-day festival features the likes of bestselling whodunit author Anthony Horowitz, Peter and Dan Snow’s Treasures of British History and astronaut Chris Hadfield, talking about his new children’s book, plus many more.

What to wear

The event will be abuzz with young professionals, intellects and millennials, so you’ll need something suave yet understated to stand out from the crowd. The luxurious two toned coat from Les Filles D’ailleurs goes perfectly with a delicate silk dress from Privatsachen and a pair of grey suede heels from The Last Conspiracy. Click here to get the full outfit.

Outfit put together by Olivia May for Cheltenham Literature FestivalOutfit put together by Olivia May for Cheltenham Literature Festival

3. Silurian Choir, Pershore Abbey

29 October, 7.30pm

The Anglo-Saxon Pershore Abbey promises to be an atmospheric setting for an evening of enchanting 18th-century music, performed by the talented Silurian Choir. As the Worcestershire-based singers offer a range of composers and styles, the musical line-up includes Bach, Handel, William Boyce’s Oh Where Shall Wisdom Be Found? and songs from Thomas Arne, the man behind Rule Britannia.

What to wear

A concert like this requires one to dress in a sophisticated manner and we know just the outfit. A long gingham skirt teamed with a short ivory jacket embossed with a unique floral pattern, both from Les Filles D’ailleurs, is the perfect attire for the evening. Keep your feet warm in the abbey with a pair of comfortable ankle boots. Click here to get the full look. Click here to get the full look.

Outfit put together by Olivia May for a performance by The Silurian ChoirOutfit put together by Olivia May for a performance by The Silurian Choir

4. The Open, Cheltenham Racecourse

11-13 November

The Open at Cheltenham’s world-renowned racecourse is one of the most popular events in the horse racing season. There is a wonderful atmosphere throughout the three days of races, which begins with Countryside Day where there are also plenty of countryside pursuits to enjoy. The second day, BetVictor Gold Cup Day, comprises the most anticipated races in Cheltenham outside The Festival, before things draw to a close with The Open Sunday.

What to wear

It can be some achievement combining stylish with practical, but this dotty jacket from Lilith is perfect for a warm and sophisticated layered look. It can be worn over a long sleeved dress and looks great with a pair of high heels. Don’t forget a fascinator if you really want to impress. Click here to get the full look.

Outfit put together by Olivia May for The Open at Cheltenham RacecourseOutfit put together by Olivia May for The Open at Cheltenham Racecourse

5. Bath Christmas Market

24 November to 11 December

The festive season arrives in the Cotswolds with the launch of Bath’s famous Christmas Market. The historic streets are transformed as hundreds of chalets spring up, festooned with lights. If you go to shop, you will be spoiled for choice with the beautifully handcrafted products made by local and independent stallholders. Then when it’s time for a rest, enjoy a mulled wine and a mince pie while listening to carols.

What to wear

This long coat from Rundholz Black Label is a trendy buy and perfect for keeping toasty on a cold winter’s day while browsing through the market. For those extra crisp days, add the faux fur snood also from Rundholz Black Label. Click here to get the full look.

Outfit put together by Olivia May for Bath Christmas MarketOutfit put together by Olivia May for Bath Christmas Market

6. Treetop walkway, Westonbirt

There are few places better to experience autumn’s stunning colours than Westonbirt Arboretum, and it is now possible to get even closer to nature with the recently opened treetop walkway. It reaches up 13 metres at its highest and has interactive activities so children can learn more about this leafy kingdom.

For those who prefer to keep their feet firmly on the ground, Westonbirt has acres to explore and 15,000 trees from all over the world. So pack a camera and tasty picnic, choose one of the many tracks and get back to nature.

What to wear

This cosy yet feminine look was put together by Olivia May and it is a superb ensemble for long afternoon walks in the arboretum with the crunchy leaves at your feet and chill in the air. The spotted scarf compliments the gingham swing dress from Les Ours perfectly. Click here to get the full look.

Outfit put together by Olivia May for an autumn walk at WestonbirtOutfit put together by Olivia May for an autumn walk at Westonbirt

7. Spa weekend, Dormy House

This is one for when the weather turns grey and wet. Only a stone’s throw from the picturesque Cotswold town of Broadway, Dormy House can be found on the Farncombe Estate, where the ‘Scandinavian meets Cotswolds’ spa is a truly indulgent affair. Start off with a relaxing dip in the candlelit infinity pool before reclining in the tranquil thermal suite. Then finish your visit with a soothing ‘back classic’ massage in the Suite of Treats.

What to wear

After a day of pampering and luxury, make your way to The Garden Room restaurant in the hotel to indulge in a main course from the à la carte menu. For this formal affair, try the high neck midi dress from Crea Concept, best suited with a clutch bag and a pair of high heels. Click here to get the full look.

Outfit put together by Olivia May for a spa weekend at Dormy HouseOutfit put together by Olivia May for a spa weekend at Dormy House

8. In the field

If you like a brisk and refreshing walk through a field with your four-legged friend, then the Cotswolds boasts countless opportunities. The shooting season is almost upon us, and it’s a great time to get out, be social and enjoy the hobby with other like-minded individuals. After a bracing day, regroup with elevenses and a game supper.

What to wear

Warm clothing in pretty autumnal colours of deep prune, olive green and buttery cream will make for a distinguished country look. We love this oversized dropped hem shirt and vintage waistcoat from Ewa I Walla. Click here to get the full look.

Outfit put together by Olivia May for a day out in the fieldOutfit put together by Olivia May for a day out in the field

Like what you see? All outfits, plus many more are available at Olivia May boutique online or in store:

31 Little Clarendon street, Oxford OX1 2HU

Olivia May, OxfordOlivia May, Oxford

For any enquiries please call or email:

01865 515 336

*Disclaimer: the events and venues mentioned in this article were not paid to be included


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