Reaper’s Rum launches ‘Reaper’s Run’, a Halloween 5K in Anstruther

Reap the Night | Saturday 31 October 2026 | 3.00pm | The Ship, Anstruther

Reaper’s Rum is bringing some Halloween spirit to Anstruther with Reaper’s Run, a new 5K taking place on Saturday 31^st October 2026.

Organised by Reaper’s Rum, which owns The Ship pub in Anstruther, the run starts and finishes outside The Ship. Runners will complete three laps of a route around the harbour and up Lovers Lane, covering 5K in total.

The route isn’t just for the views. Lovers Lane gives a nod to The Lovers, one of Reaper’s Rum’s own expressions, while looping the harbour reflects the family’s roots in Anstruther’s fishing community.

With a 3pm start, the race makes the most of the last of the daylight while keeping the Halloween atmosphere going into the evening.

Fancy dress is very much encouraged, with prizes for the best Halloween costumes, while every finisher will receive a specially commissioned Reap the Night Halloween medal.

There’s plenty more up for grabs too. The male and female race winners will each take home a bottle of Reaper’s Rum, and runners should keep an eye out for spot prizes along the route, including Reaper’s Rum hoodies.

There’ll be music down at the harbour to keep runners going as they make their way round the course.

Once the running’s done, the celebrations carry on at The Ship. Everyone taking part with a race bib can claim a free Reaper’s Rum at the pub after the race. Reaper’s Run is as much a Halloween party as it is a 5K.

Allan Drysdale, owner of The Ship and Reaper’s Rum, said: “Anstruther is a beautiful place to bring people together, and this route means a lot to us personally. It runs right past the harbour similar to where my mum’s family fished for generations in East Neuk, and the reaper on our bottles felt made for Halloween. We added Lovers Lane in for a reason too: it’s a tough climb, but worth it, much like the best love stories.”

Reaper’s Rum wants runners to get creative with their costumes, bring their friends and come ready to run, race and Reap the Night in Anstruther. Under 18’s are welcome, but must be accompanied by an adult and will be offered a soft drink rather than alcohol at the finish.

Event details

Reaper’s Run – Reap the Night Halloween 5K

📍 The Ship, Anstruther 

📅 Saturday 31 October 2026 

⏰ 3.00pm start 

🏃 5K / 3.1 miles 

🎃 Halloween fancy dress encouraged 

🏅 Halloween medal for all finishers 

🏆 Spot prizes  

🥃 Reaper’s Rum for race winners and free drinks at the Ship for bibbed runners 

🎵 Music on the harbour 

£12 entry fee which is redeemable for Reaper's Rum at The Ship. All profits will be donated to the RNLI. 

Entries close on Thursday 29th October. Refunds will only be available if we can transfer your place to someone on our waiting list before entries close on Thursday 29th October. Any refunds will be provided less £1 EntryCentral fees. Registration and number collection will be on the day at The Ship between 1-2:45pm.

Parking

Parking in Anstruther can be tricky. We recommend using the car park behind the Coop and jog to the race start. https://maps.app.goo.gl/e3ywimCc1wS6634b9 There is on street parking but places will be limited.