Our Favourite Things to Do in Rutland

November in Rutland is a time of crisp walks, glowing bonfires, and the first glimmers of Christmas magic. From exciting outdoor adventures to cosy festive markets, Oakham and its surrounding countryside offer plenty to see and do as the year draws to a close.

Here’s our round-up of the top things to do in Oakham and Rutland in November 2025 — perfect for locals, visitors, and anyone looking to enjoy the very best of England’s smallest (and friendliest) county.

October is a magical month in Rutland — the countryside glows with autumn colours, cosy events fill the calendar, and Halloween fun brings families together. Whether you’re looking for seasonal walks, cultural evenings, or pumpkin-picking adventures, Oakham and Rutland have something for everyone.

Here’s your guide to what’s on throughout the month.

Looking for the best things to do in Oakham and Rutland this September? As the summer draws to a close and Autumn peeps round the corner, September is the perfect time to explore Rutland’s rolling countryside, historic landmarks, and vibrant local events. Whether you’re a lover of sport, food, or culture, there’s something for everyone this month including world-famous horse trials to lakeside triathlons and vibrant festivals. Here are the highlights of the top Rutland events in September 2025 to look forward to:

August in Oakham, Rutland is brimming with exciting events, family-friendly activities, and plenty of reasons to get out and enjoy the summer. Whether you're a foodie, a flower enthusiast, a dog lover, or an adventurer seeking something different, this charming market town and its beautiful surroundings have something for everyone. Here's your ultimate guide to what's on in Oakham and the wider Rutland area this August 2025.

Rutland might be England’s smallest county, but it doesn’t hold back when it comes to summer events. From world-class wildlife gatherings to lakeside Shakespeare and Sunday music in the park, there’s plenty going on in and around Oakham this July. Here’s your essential guide!

As summer arrives in full bloom, the picturesque county of Rutland and its historic town Oakham come alive with events, activities, and opportunities to soak in the season. Whether you’re into country shows, local ales, live music, or scenic walks, June 2025 has something for everyone. Here's your curated guide to the best things happening in the Oakham and Rutland area this month

May in Rutland is when the countryside wakes up, the events calendar fills out, and there’s no excuse to stay indoors. Whether you’re into vintage cars, watersports, cider, or country sports, Oakham and the wider Rutland area have you covered this month. Here’s your shortlist of things worth visiting for.

With so many top attractions on our doorstep you will be spoilt for choice of what to do. Please see a list below of our top recommendations to make your stay one to remember...