Dating Ideas for October
As the leaves turn golden and the nights draw in, autumn in London offers endless opportunities for cosy and adventurous dates.
If you’re dating in your 30s or 40s and looking for something unique to do in London (or just outside), these autumn date ideas are the perfect way to spend quality time with someone special. Whether you’re into nature, film, or seasonal festivities, these four itineraries offer a great mix of activities, food, and culture—with a focus on convenience, safety, and memorable experiences.
If you’ve got a dating idea we should be writing about, email laura@twelvestories.co to let us know.
Credit Torsten Dederichs.
For Wanderers, Roast-Lovers & Nature-Watchers
Mini Dating Itinerary 1: Richmond Park Deer Watching + Cosy Pub Meal
Nothing says autumn quite like a crisp walk through Richmond Park, especially during deer rutting season. This is a chance to experience London’s wildlife in all its natural beauty, with plenty of conversation starters as you spot deer roaming freely.
Morning/Afternoon: Start your day at 10 AM with a stroll through Richmond Park, beginning at Pembroke Lodge for stunning panoramic views. Head towards Pen Ponds to watch the deer in their element during rutting season.
Lunch: After your walk, unwind at The Roebuck, a cosy pub in Richmond offering hearty comfort food with views over the Thames. A Sunday roast or shared dessert will cap off your nature-filled date perfectly.
Travel Links: Richmond Park is a 15-minute walk from Richmond Station, which is on the District Line, Overground, and South Western Railway.
Safety Tip: Plan to leave the park before dusk, around 4:30 PM, when it closes.
For Film Buffs & Cocktail Enthusiasts
Mini Dating Itinerary 2: A Visit to the London Film Festival + Cocktails
For cinema lovers and culture seekers, the BFI London Film Festival on the South Bank is an ideal autumn date. It offers a chance to watch critically acclaimed films from around the world, with the excitement of being part of one of London’s premier cultural events.
Late Afternoon/Evening: Pick a 4 PM screening at the BFI, then take a scenic walk along the South Bank. Post-film, you can continue the conversation at Lyaness, a chic cocktail bar located at Sea Containers, where the views are as enticing as the drinks.
Travel Links: The BFI is a 5-minute walk from Waterloo Station or Blackfriars Station.
Safety Tip: The South Bank remains lively into the evening, but aim to head home around 9 PM for a safe and convenient journey.
For City Adventurers & Skyline Dreamers
Mini Dating Itinerary 3: Rooftop Cinema at the Bussey Building, Peckham
If you’re looking for a fun, nostalgic date night with a twist, Rooftop Cinema Club in Peckham is perfect for autumn. Cosy up with blankets, enjoy a seasonal film under the stars, and take in stunning views of the city skyline.
Early Evening: Kick off the evening with a drink and small plates at Forza Wine, located in the Bussey Building itself. Arrive by 6 PM to catch the sunset over London before heading down to the rooftop cinema for an 8 PM screening.
Travel Links: The Bussey Building is just a short walk from Peckham Rye Station, accessible via Overground and Southern Rail.
Safety Tip: Wrap up by 11 PM and use well-lit streets on your way to Peckham Rye station, where public transport is frequent and easy to access.
For Autumn Enthusiasts & Countryside Explorers
Mini Dating Itinerary 4: Pumpkin Picking at Crockford Bridge Farm + Cosy Autumn Dinner
For an out-of-town experience that celebrates the best of autumn, a trip to Crockford Bridge Farm for pumpkin picking is a fun and seasonal date idea. You’ll get to enjoy the fresh countryside air and take home your own handpicked pumpkins to carve or cook with later.
Morning/Afternoon: Arrive first thing to pick your pumpkins and explore the farm’s Pumpkin Festival (on select weekends). It’s an ideal way to embrace the season, with a touch of playful fun.
Lunch: After your farm adventure, head to The Cricketers in Row Town, just 5 minutes away, for a warm and hearty meal. Whether you choose a traditional Sunday roast or opt for their autumn specials, the cosy pub vibe will help you unwind after your day out.
Travel Links: Located just under an hour from central London by car. For those using public transport, West Byfleet Station is the nearest, with a quick 5-minute drive from the farm. Trains run directly to London Waterloo in around 40 minutes.
Safety Tip: Plan your return journey for 4 PM to ensure you're travelling home during daylight hours.
Autumn is one of the most romantic seasons in London, and these date ideas are perfect for people in their 30s and 40s looking to enjoy the best of the season.
Whether you’re watching the deer in Richmond Park, catching a movie at the BFI, or picking pumpkins at a nearby farm, each itinerary is designed to create lasting memories. With travel links and safety tips included, you can focus on enjoying each other’s company without the worry of logistics.
So, grab your coat, embrace the season, and make this autumn one to remember.
Safety advice: please always let at least one extra person know where you are on your date, different times and locations, and arrange moments to check in. Plan your travel carefully, make sure you’re in control of getting there and getting away. And if you’re in any doubt - seek help from any employee as part of 'Ask for Angela’, or ask a member of the public if that’s not possible.
Forza Wine, Peckham. Credit The Nudge.