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Hikes
United States
Hawaiʻi County

Kailua

The best walks and hikes around Kailua

4.6

(40)

746

hikers

20

hikes

Hiking around Kailua offers a range of trails primarily characterized by coastal paths and urban loops. The region features relatively flat terrain with minimal elevation gain, making it accessible for various activity levels. These routes often provide views of Kailua Bay and pass through local points of interest. The landscape is defined by its proximity to the ocean and developed areas.

Best hiking trails around Kailua

  • The most popular hiking route is Kailua-Kona – Mokuaikaua Church loop from Puapuaʻa Point, a 5.4 miles (8.6 km) trail that takes 2 hours 17 minutes to complete. This moderate path features coastal views and passes through the town center.
  • Another top favourite among local hikers is Mokuaikaua Church – Kailua-Kona loop from St. Michael the Archangel Parish, an easy 4.2 miles (6.7 km) path. This route offers a pleasant walk along the bay and through historical areas.
  • Local hikers also love the Kailua-Kona – Mokuaikaua Church loop from St. Michael the Archangel Parish, a 3.7 miles (5.9 km) trail leading through urban and coastal landscapes, often completed in about 1 hour 32 minutes.
  • Hiking around Kailua is defined by coastal paths, urban loops, and historical points of interest. The network offers options for different ability levels, from easy strolls to moderate walks.
  • The routes in Kailua are highly rated by the komoot community with an average score of 4.5 stars from over 30 reviews. More than 600 hikers have used komoot to explore Kailua's varied terrain.

Last updated: April 27, 2026

46

hikers

#1.

Mokuaikaua Church – Kailua-Kona loop from St. Michael the Archangel Parish

6.73km

01:45

50m

50m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

Moderate

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Popular around Kailua

Running Trails around Kailua

Road Cycling Routes around Kailua

Cycling around Kailua

Tips from the Community

Puffin
April 8, 2025, Mokuaikaua Church

Founded in 1820, the church is the oldest church in Hawaii

Translated by Google

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Puffin
April 8, 2025, Huliheʻe Palace

small museum in the former summer residence of the royal family

Translated by Google

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some great fruit and veggies and clothes

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Micky Wartena
March 25, 2025, Kailua Bay

a must see

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2

Christopher
October 27, 2023, Kailua-Kona

Come see the beaches of Kona and enjoy the renowned coffee, ride the same course as professional triathletes, and kick back at one of the many restaurants available within pedaling distance!

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Christopher
October 27, 2023, Huliheʻe Palace

In 1924 this historic building was in ruins and dilapidated. Like much of the low income housing in the midwest, this property could not even be seen from the road. The property was owned by the Daughters of the Territorial Legislature and even after pressure to sell the valuable land the building was on, they held strong and eventually the building was restored many years later. Inside, there are old artifacts and furniture to show Hawai‘i's royal past.

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Ali‘i Garden Marketplace is a great stop on a ride to grab a bite from one of the 20+ vendors available in this open-air market. In addition to food, there is plenty of shopping and free wifi!

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oliviakellis
October 24, 2023, Kailua Bay

This beautiful spot is perhaps best known as the starting point for the grueling swimming portion of the annual IRONMAN World Championship triathlon. When not hosting this iconic sporting event, Kailua Bay dazzles with its postcard-worthy scenery. Whether you're a triathlete or a leisurely runner, you'll enjoy running along this charming bay nestled on the sunny shores of paradise.

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Frequently Asked Questions

What types of hiking trails can I find in Kailua?

Kailua offers a variety of trails, primarily characterized by coastal paths and urban loops. The terrain is generally flat with minimal elevation gain, making it accessible for many activity levels. You'll find routes that provide views of Kailua Bay and pass through local points of interest.

How many hiking routes are available in Kailua?

There are 18 hiking routes available in Kailua, with 14 rated as easy and 4 as moderate. There are no difficult trails listed, making the area suitable for a wide range of hikers.

Are there any family-friendly or easy hikes in Kailua?

Yes, Kailua is well-suited for family-friendly and easy hikes. Most of the trails are rated as easy, such as the Mokuaikaua Church – Kailua-Kona loop from St. Michael the Archangel Parish, which offers a pleasant walk along the bay and through historical areas. These routes are generally flat and accessible.

What are some notable natural features or viewpoints along Kailua's trails?

While Kailua's immediate trails focus on coastal and urban views, the broader Oahu region is known for stunning natural features. For panoramic ocean views, the famous Lanikai Pillbox Hike (Kaiwa Ridge Trail) is a highlight. For lush rainforests and waterfalls, consider the Maunawili Falls Trail. These offer diverse natural experiences beyond the immediate Kailua urban paths.

What do other hikers enjoy most about hiking in Kailua?

The hiking routes in Kailua are highly rated by the komoot community, with an average score of 4.5 stars from over 30 reviews. Hikers often praise the accessible coastal views and the opportunity to explore historical areas within the town.

Are there any circular routes in Kailua?

Yes, many of the routes in Kailua are designed as loops. For instance, the Kailua-Kona – Mokuaikaua Church loop from Puapuaʻa Point is a moderate 8.6 km trail that takes you through coastal views and the town center, returning to your starting point.

What historical or cultural landmarks can I see while hiking in Kailua?

Several trails in Kailua pass by significant landmarks. You can explore sites like the Huliheʻe Palace, a former vacation home for Hawaiian royalty, or the historic St. Peter's Catholic Church. The routes often weave through the Kailua-Kona settlement itself, offering a glimpse into its rich history.

Are there any trails that offer a true immersion in Hawaii's natural beauty, like rainforests or waterfalls?

While the immediate Kailua trails are more coastal and urban, the broader Oahu region offers such experiences. The Maunawili Falls Trail, for example, provides a trek through a lush rainforest culminating in a picturesque waterfall and natural swimming hole, offering a deeper immersion into Hawaii's natural landscapes.

What is the best time of year to go hiking in Kailua?

Kailua, located on the windward side of Oahu, generally offers pleasant hiking conditions year-round due to Hawaii's tropical climate. However, the cooler, drier months from April to October are often preferred for outdoor activities, avoiding the slightly wetter winter season.

Are there any challenging hikes for experienced adventurers near Kailua?

For more experienced adventurers seeking a challenge, the Olomana Three Peaks Trail, often called the 'Everest of Kailua,' is a strenuous and technical hike offering breathtaking 360-degree views of the Windward coast and the Ko'olau Range. This is a significant step up from the moderate trails found directly within Kailua.

Can I find trails suitable for birdwatching in Kailua?

Yes, for a tranquil experience and excellent birdwatching opportunities, the Kawainui Marsh Trail is a flat, approximately 3-mile path through Hawaii's largest wetland. It offers striking windward mountain views and is a haven for four endangered native Hawaiian waterbirds.

Are there any trails that offer views of the Mokulua Islands?

Yes, the iconic Lanikai Pillbox Hike (Kaiwa Ridge Trail), though relatively short, is famous for its spectacular sunrise views over the Mokulua Islands. It's a popular choice for those seeking stunning coastal vistas.

Most popular routes around Kailua

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