40 years of Acorn Awards: The 2000s – Caroline Gregory

Throughout four decades, the Acorn Awards, in partnership with CH&Co, have helped spotlight talent that has gone on to shape the hospitality industry. 

The prestigious awards, which celebrate 30 people under the age of 30, working back or front of house in the UK hospitality industry, are now in their 40th year – an extra-special milestone celebrating the brightest young talent shaping hospitality at an early stage in their careers. The Acorn Award winners are invited on a special weekend away in a hotel somewhere in the UK, where they take part in group activities and receive their trophies after a celebratory lunch. 

Ahead of the 2026 winners’ weekend this week, The Caterer is looking back and speaking to a winner from each decade to ask them about what winning meant to them, how it shaped their career today and what top tunes they were dancing away to on the night of their win.

For the noughties cohort, we spoke to Caroline Gregory, who returns to the Acorn Awards this year as keynote speaker.

Gregory has spent the majority of her career at the Lovat in Fort Augustus, formerly called the Lovat Arms. She joined the Highland hotel in 2005 and progressed to managing director. 

Alongside her operational role, she has been a longstanding champion of skills development in Scottish hospitality, serving as a Highlands committee member for HIT Scotland from 2011-2022. Since 2024, she has also chaired Apprenticeship in Hospitality Scotland, a partnership of leading hospitality businesses dedicated to attracting, developing and retaining the next generation of talent. The initiative’s partners include Gleneagles, Cameron House and Kimpton Blythswood Square.

Here Gregory reflects on an Acorn winners’ weekend held in a former prison, how receiving the award transformed her confidence and why young hospitality professionals should embrace every stage of their career journey.

Who nominated you?

Marina Huggett, chairperson at the Achnagairn Estate near Inverness. She runs her own business, Tourism Excellence Consultancy, and is a tourism professional.

Where was your winners’ weekend and what was your task?

It was at the Malmaison Oxford, which is located in a converted prison. It didn’t feel like a prison, but when you stripped everything back, you could see the signs. I remember the bedroom windows were so high up you couldn’t look out of them and the rooms were relatively dark, but in a very atmospheric and beautiful way. It really was an amazing venue. 

Our activity was a history hunt around the town. We were split into four teams and we all had to wear coloured caps. We were oblivious to tourists – it was just us mad people running around the town doing our thing. I don’t think we got anything for it – it was really just a bit of fun and a whirlwind 24 hours.

Can you recall the moment you received your Acorn Award? 

I still have the two photos from the ceremony in my office – a professional one and one of me being a bit silly. It was a joyous moment and very humbling at the same time. I felt so proud to be in this elite group of 30 industry mavericks. 

I remember speaking to the then editor of The Caterer, Mark Lewis. To have that direct contact with people in the industry that you had always seen as a photo in a magazine, to suddenly to be sitting and having a drink with him, I thought: “Wow, OK, this is achievable. This is attainable”. Because of that communication with him, we had an editorial in The Caterer about the hotel and its F&B, which was great.