Last Updated: 12th Nov 2023

Beginner - Intermediate

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I've done it Done

Pineapple and Flagstaff

Dunedin, Otago

Submitted by Kieran Philip

Last Updated: 12th Nov 2023

Beginner - Intermediate

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I've done it Done


Grunt Factor: 12 ?

Gnarl Factor: 28 ?








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Trail Map

Type of Run


Out and Back

Very hilly

Dog Friendly

Native bush

Open tussock/grasslands

Open ridges/tops

Run Makeup


Gravel Road

Easy Single Track

Moderate Single Track

Technical Single Track

Average Uphill Gradient: +14.0%

Average Downhill Gradient: -13.9%


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Estimated Times to Run







Starting at the base of the hill, Tanner Rd, follow the well marked track up the hill. It heads up past a water fountain (handy spot to fill up if you are planning on going further afield). You then pass by the Water Treatment station (to the hight hand side of the buildings) and head in a lovely section of native bush. You wind your way up through this and then break out onto the open areas. Continue heading forward until you reach the junction signpost where you can also head to Swampy Summit if you choose. Take a left here and head towards Flagstaff as you wind around the closest hill. Continue on, you know you've reached Flagstaff when you reach the plaque/survey mark at the top. Then it's a nice gentle meander back down, or a blistering quad-smashing speed back down, either way will get you back to your car.

This trail includes the peak Flagstaff.

360 degree panoramic views of surrounding countryside - which is well worth a look!

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Parking available in the streets around the starting location.

6 km

13 minutes




Perfect throughout.

Long-sleeved thermal top, Windproof jacket, Gloves, Beanie/thermal headwear, Whistle, First aid kit, Extra food for emergencies, Cellphone, Map

Water fountain near the bottom of the track, none higher up.

Can be rather windy and chilly up on top, with snow at times during winter. Pack windproof clothing.

Trail Legend


julie stewart

has completed Pineapple and Flagstaff 4 times in the last year.

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Trail Reviews

Tough wee climb but we'll worth it for the views and the downhill!!

Adam Clifford

August 19, 2022

Steep Dunedin hills. I did this on a beautiful day with no wind and clear skies. Amazing views from the top. Well worth the effort. Well maintained trail.

Suzanne Roberts

April 16, 2021

Tough and enjoyable.

Tom Sweeney

January 8, 2021

I was lucky and choose the only hill not in clouds the day went up. Great views of the city

Paul Forbes

May 4, 2020

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Overlapping Trails

These overlap with this trail to some degree. You may wish to combine them but please note that to qualify for FKTs on these runs you should record a separate activity for each.

Green Hill via Swampy

Green Hill via Swampy

Length: 30.0km

Level: Intermediate

Alternative Flagstaff Circuit

Alternative Flagstaff Circuit

Length: 14.4km

Level: Intermediate

Ross, Pineapple, Frasers loop

Ross, Pineapple, Frasers loop

Length: 18.5km

Level: Beginner - Intermediate

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