You know where most of the local people go to get their fix of nightlife? Las Vegas. After that it’s Honolulu, then Maui. Most of the entertainment on Moloka‘i is of the live music variety, and that usually means that it’s going to be traditional island music played in a kanikapila style (island jam session, get-together, talk story). Witnessing a live jam session can be captivating and a true island experience.
While there can often be impromptu ukulele sessions which pop up during the weekdays on the porch outside of the Coffees of Hawaii Espresso Bar (1630 Farrington Ave., 6am-5pm Mon.-Fri., 8am-8pm Sat., 8am-5pm Sun.), Sunday afternoons are when things on this laid-back wooden deck get hopping. Hawaiian and contemporary music is played live 3pm-5pm, so this is the de facto social gathering for a late Sunday afternoon.
The Kualapu‘u Cookhouse (102 Farrington Ave., 808/567-9655, 7am-8pm Mon.-Sat., 9am-8pm Sun.) also has live music on Thursday afternoons at 5pm to accompany the weekly dinner specials.
The longest running and most iconic show on the island is the performance of Na Kupuna 4pm-6pm on Friday afternoons at Hotel Moloka‘i (1300 Kamehameha V Hwy., 808/660-3397). Kupuna is a Hawaiian word meaning elder, and children are taught that kupuna are to be revered and treated with respect—something easy to do when it comes to the musical capabilities of the island’s most well-known band. Sit out on the well-manicured grounds of the hotel and enjoy a mai tai or a Longboard Lager while listening to these guys play. They offer more than simply music; the personal anecdotes, humorous stories, and island-style banter that accompany the songs all combine to make a Na Kupuna performance the best evening on Moloka‘i.
Even on sleepy Moloka‘i there is still “ladies night.” Once the late afternoon ukulele performances are through and you feel like a few more beers, Paddler’s Inn (10 Mohala St., 808/553-3300, 11:30am-11pm Mon.-Sun) is the closest thing that you’re going to get to a sports bar or a dance hall on all of Moloka‘i. On the side of the highway in downtown Kaunakakai, you’ll find this place with a couple of pool tables occupying the interior while a full-service bar sits in the outside lanai. There are live bands some nights of the week, top 40 music on others.
Other than Paddler’s, the only other option in town is the bar at Hotel Moloka‘i (1300 Kamehameha V Hwy., 808/660-3397). While a kitchen fire closed the restaurant for 2013 and the bar currently closes early, once the restaurant reopens (no current word on when), the bar will be moved to the ocean side of the resort and potentially stay open until 2am. Inquire with the hotel about the current status.