Explore the Wairarapa Five Towns Trail

Wairarapa Valley Cycleway

Masterton to Featherston via Martinborough
A trail by New Zealand Cycle Trails
50 KM
Advanced
Masterton / Wairarapa Moana

Trail Details

The Wairarapa Valley Cycleway offers a gentle, rewarding journey through some of the region’s most picturesque rural landscapes, linking the northern township of Masterton with the wine village of Martinborough. Beginning in Masterton, the route meanders
through quiet country roads, open farmland and the small settlement of Gladstone, where riders can pause for refreshments at our locally famous Gladdy Inn before continuing south.

As the trail moves toward Martinborough, the scenery shifts into classic Wairarapa wine country. Vineyards, rolling hills and leafy lanes guide you into the village square, where cellar doors, tastings and relaxed dining options give the ride a distinctly indulgent finish. The trail also connects with safer alternative routes toward Featherston and the Remutaka Cycle Trail, offering riders flexibility to extend their adventure. Ideal for those seeking a full-day outing with varied scenery and plenty of opportunities to explore along the way, the Wairarapa Valley Cycleway is an inviting way to experience the depth and charm of the region.

For further trail specifics, see Wairarapa Valley Cycleway.

Perfect for all kinds of explorers

Touring Cyclists
This 50 km grade 4 (advanced) route is ideal for riders with average fitness. Gentle undulations and mostly flat terrain make it suitable for road, touring, or e-bikes. Basic mechanical skills are recommended, and riders should carry a small toolkit and spares.

Scenic & Leisure Riders
Soak up panoramic views of Wairarapa farmland, vineyards, and the distant Tararua Range. The route passes through charming villages like Gladstone and Martinborough, offering plenty of opportunities to stop for wine tastings, food, or photos.

Adventure Seekers
Connect to the Remutaka Cycle Trail at Western Lake Road for a thrilling ride along the rugged Wairarapa coast. Alternatively, explore side routes such as the Lake Ferry detour or Route 52 north from Masterton.

Trail highlights:

  • Length: ~50 km (Masterton → Western Lake Road)
  • Difficulty: Advanced
  • Surface: 100% sealed road
  • Access Points: Masterton, Gladstone, Martinborough, Featherston, Western Lake Road
  • Amenities: Food, water, and toilets available in Masterton, Martinborough, and Featherston; picnic spots and wineries along the way

Experience the best of Wairarapa

Start in Masterton, cycling east along Church Street and Colombo Street before joining Te Whiti Road toward Gladstone. Take a short detour to the Gladstone Inn for a snack or overnight stay. Continue along Longbush Road and Hinakura Road into Martinborough, the heart of Wairarapa wine country. Explore the leafy village centre, enjoy cellar-door tastings, or relax in one of the cafés.

From Martinborough, bypass the busy SH53 by taking Jellicoe Street and Lake Ferry Road southwest, then continue on Kahutara Road and East West Access Road toward Western Lake Road, where the trail meets the Remutaka Cycle Trail along Lake Wairarapa. Here, you can choose to follow the coast, continue to Featherston, or connect with other regional cycling routes.

The Wairarapa Valley Cycleway showcases quintessential rural landscapes, vineyards, rolling farmland, and distant mountain views, offering a full-day or multi-day adventure depending on your pace and stops.

Know before you go

  • Weather: Ride all year round, but be prepared for sudden rain.
  • Navigation: Well-signed, but carry a map to identify points of interest and avoid wrong turns.
  • Safety: Roads near Masterton and Martinborough can have moderate traffic. Be alert and follow NZ cycling rules.
  • Food & Water: Available in Masterton, Martinborough, and Featherston; river water should be boiled or treated.
  • Toilets: Public toilets in main towns.
  • Cellphone Coverage: Patchy in rural sections.
  • Transport: Trains run to Featherston and Masterton from Wellington; intercity buses service Masterton. Local buses run between Martinborough and Featherston.

This trail links to…

Loop Around the Lake – shares sections of the route via Featherston and Kahutara Road.

Martinborough Trails – head into Martinborough for vineyard loops and onward rides.

Connects into Featherston trails for access to the Remutaka Cycle Trail the Tauwharenīkau Trail and the Greytown Rail Trail.

Suggested Itinerary

Morning: Coffee & Breakfast in Masterton
Mid-Morning: Cycle Through Gladstone
Afternoon: Explore the Scenic Countryside
Late Afternoon / Evening: Featherston & Return Options

Trail Weather

Additional info

Start your journey in Masterton or join the trail along quieter sections through Gladstone or Martinborough, continuing southwest toward Western Lake Road, where it intersects the Remutaka Cycle Trail. The sealed route is suitable for road bikes, touring bikes, e-bikes, and leisure cyclists.

Travelling to Wairarapa by train? Visit Metlink to plan your trip. Featherston and Masterton stations provide easy access to the start or intermediate points of the trail.

  • Length: ~50 km (Masterton → Western Lake Road)
  • Difficulty: Advanced
  • Access Points: Masterton, Gladstone, Martinborough, Featherston, Western Lake Road
  • Amenities: Food, water, and toilets available in Masterton, Martinborough, and Featherston; picnic spots and wineries along the way

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