On Sunday, October 18, 2026, Ali'i Drive hosts two afternoon events about 14 trolley minutes apart. The Kokua Kailua Village Stroll closes Historic Kailua Village to cars from 1 to 6 p.m. The 29th Annual Hawaiian Slack Key Guitar Festival – Kona Style plays from 1 to 5 p.m. at OUTRIGGER Kona Resort & Spa in Keauhou, with doors opening at noon.
The two events overlap for four hours. The stroll runs one hour longer at the north end, and the county's Route 201 trolley runs hourly between the stroll's southern edge and Keauhou. Those two facts point in different directions. Seeing the festival first means you miss less of either event. Starting at the stroll means you only park once.
The village keeps going for one more hour
Kokua Kailua happens once a month on a Sunday. The village becomes a pedestrian-only market stretching from Kailua Pier through Historic Kailua Village to Hualālai Road, with more than 100 vendor booths for local artisans, crafters, musicians and merchants, plus places to eat. Leashed dogs are welcome. The October 18 date is on Historic Kailua Village's 2026 schedule. November 15 is next, and December 13 is the Kailua Kalikimaka edition.
October has no concert listed. The September 20 stroll had the fall concert. The organizer hasn't posted a vendor or music lineup for October, so expect the regular stroll without a headline act.
The festival ends at 5. A festival-goer who heads back north still reaches the village while the booths are open. The reverse doesn't work. If you leave the stroll at 2:30, you've missed the first stretch of a four-hour show that started at 1.
Fourteen minutes, on the hour
Hele-On's Route 201 is the Ali'i Drive circulator. It runs from the Loloku Street Park & Ride to Keauhou seven days a week, every 60 minutes, from 6 a.m. to 9 p.m. The current schedule took effect July 12, 2026. Two of its southbound stops line up with this afternoon. One is on Ali'i Drive across from Hualālai Road, the south edge of the stroll closure. The other is on Ali'i Drive at Outrigger Keauhou.
| Southbound departs Ali'i Dr across Hualālai Rd | Arrives Ali'i Dr @ Outrigger Keauhou |
|---|---|
| 12:14 p.m. | 12:28 p.m. |
| 1:14 p.m. | 1:28 p.m. |
| 2:14 p.m. | 2:28 p.m. |
| 3:14 p.m. | 3:28 p.m. |
| 4:14 p.m. | 4:28 p.m. |
On the way down, the trolley also stops across from Coconut Grove Marketplace and at the Royal Kona Resort, Honl's Beach Park, Magic Sands Beach Park and Kahalu'u Beach. The stop is labeled Outrigger Keauhou and sits on Ali'i Drive. The festival's address is 78-128 Ehukai Street, so plan for the walk from Ali'i Drive to the resort.
Several Route 201 stops are inside the stretch that closes for the stroll, including Palani Road at Ali'i Drive. Hele-On posts rider alerts for changes, so check them that Sunday morning before you count on any stop between the pier and Hualālai Road. The table above covers the southbound trip. If you're riding back north after the festival, look up the northbound column on Hele-On's Route 201 page before you go.
Two ways to order the afternoon
Festival first, stroll last. This way you see the most music and catch the stroll's last hour.
- Drive to Keauhou and arrive close to noon, when doors open.
- Stay for as much of the 1–5 p.m. lineup as you want.
- Head back to the village for the stroll, which runs until 6 p.m.
- Plan on two parking stops, one at the resort and one in town.
Stroll first, festival second. This way you only park once and let the trolley handle the trip south.
- Park in town and walk the stroll when it opens at 1 p.m.
- Be at the stop across from Hualālai Road for the 2:14 or 3:14 trolley.
- Arrive at the Outrigger Keauhou stop at 2:28 or 3:28 and walk to the resort.
- Catch the second half of the lineup, then take the northbound trolley back to your car.
The second plan trades the festival's first hour or two for not having to look for a second parking spot.
What the festival ticket covers this year
The festival is ticketed. OUTRIGGER's event page links to Eventbrite, which showed $33.85 at the purchase prompt. For comparison, the Hawaii Tribune-Herald reported in October 2024 that the 27th festival had $20 door tickets, free entry for kids 12 and under, and 500 seats. Neither the seat count nor the youth price has been confirmed for 2026, so buy online before you count on a door ticket.
OUTRIGGER describes the event as family-friendly and open to all ages. It's built around ki ho'alu, or "loosen the key," the open-tuning fingerstyle that grew from guitars brought to the islands by vaqueros in the 19th century. The 2026 lineup includes:
- Brother Noland
- Sonny Lim, known for traditional slack key
- Keoki Kahumoku
- Blayne Asing
- Kahiau Lam Ho
- Ira Varize, playing Hawaiian cowboy ki ho'alu
- Stephen Inglis, with Grateful Dead tributes
- Anthony Pfluke, Ryder Briley and Kamuela Kahoano
Other acts appear with different spellings on different listings, so check the festival's Facebook page for the final order. Big Island Now's listing promises "4 solid hours" of music, which matters if you're planning to arrive halfway through. The resort's page says paid parking is available, but the Eventbrite listing says parking is free. Plan to pay unless OUTRIGGER tells you otherwise.
Parking in the village when the road is closed
The parking information for the village end is older than the event listings, so give yourself some extra time.
- County lot off Kuakini Highway near Palani Road. Big Island Now described it as free with at most 150 spaces in October 2023.
- Curb parking. The same 2023 report said free curb spots were limited and many were freight zones from 7 a.m. to 3 p.m.
- Coconut Grove and Kona Inn. In November 2024, both offered 90 free minutes to kama'āina with a Hawai'i driver's license. That's a two-year-old rate.
- Loloku Street Park & Ride. This is the start of Route 201, so you can leave your car there and ride both directions.
Check that last option against the Route 201 alerts before you rely on it. It's the only one on this list that keeps you from circling Kuakini at 1 p.m.
Ending at the Kona Inn
Both plans end in the village around dusk, and the Kona Inn Restaurant at 75-5744 Ali'i Drive is under new ownership this year. Island Restaurant Group was formed by Jackie Rey's, Harbor House and Umeke's Fish Market Bar & Grill. It bought the Kona Inn and Kona Canoe Club in the spring. The grand reopening and new menu launched June 18, 2026.
Operations vice president Michael Hofstedt told Big Island Now that the group set aside about $200,000 for the kitchen, dining room and bar. They kept the pulley-driven belt fans. Prime rib is back every night, beef Wellington is new, and chef Kaikili Roldan said locally caught fish stays at the center of the menu. On the shopping-village side of the same address, Bubba & Finns Snack Shack, Lavaka Gallery and Paradise Found Boutique are listed as coming soon, with no opening dates posted.
The Kona Seaside Shops at 75-5663 Palani Road won approval in June to demolish three of its five buildings and add a restaurant, two kiosks and a courtyard. When Big Island Now reported it on June 19, the project still needed design review, building permits and a contractor, and no construction start had been announced. As of that report, the October stroll would pass the center as it stands now.
At Hawai'i Estates, we spend a lot of time thinking about how the drive from the village to Keauhou fits into a Kona week, whether it's a Sunday like this one or a home search along Ali'i Drive. If you're curious what your place along the Route 201 line is worth, get your Instant Home Valuation and we'll go over the numbers with you, with aloha.
