The few choices for evening entertainment at least mean a lively crowd is guaranteed wherever you go. Paddlers’ Inn, on the ocean side of Highway 450 at Mohala Street (http://molokaipaddlersinn.com; 808/553-3300), is the island’s primary watering hole. The spacious indoor-outdoor restaurant and bar hosts predominantly local acts onstage most nights and Sunday afternoons, when Na Ohana Aloha plays Hawaiian music at 3pm. For the later shows, you’ll hear classic and contemporary Hawaiian music, country, even jazz, usually 6:30 to 8:30pm; some nights, a disco DJ or karaoke will keep the party going until midnight.
Most nights of the week, Hawaiian music enlivens Hiro’s Ohana Grill, the oceanfront/poolside bar and restaurant at Hotel Molokai. On Thursdays, live music (plus the prime rib) draws patrons to Kualapuu Cookhouse. Finally, while it’s not nightlife, per se, the twice-weekly kanikapila (jam session) at Coffees of Hawaii, 1630 Farrington Hwy. (www.coffeesofhawaii.com; 808/567-9490) is definitely worth attending. A group of ukulele-strumming aunties and uncles fill the broad lanai, playing American and Hawaiian standards. The island’s sweet-voiced kupuna (elders) dress up for the occasion and Hawaii’s best musicians drop in whenever they’re on island to croon alongside them. Don’t miss it: Tuesday mornings 10am to 1pm and Friday afternoons 3pm to 6pm.
If possible, time your trip to coincide with Ka Hula Piko ★★★ (www.kahulapiko.com), an intimate celebration of the ancient art of hula. Over three days, hula practitioners offer powerful chants and dance, not as performance but as gifts to their ancestors. This hula is unlike anything you’ll see elsewhere: dances mimicking mythological turtles, honoring the work of taro farmers, and proclaiming ancient prophesies. The island-wide festivities typically occur in the first week of June and wrap up with an all-day ho‘olaule‘a (festival) during which visiting hula troupes from as far as Japan and Europe share their skills.
The annual Ka Molokai Makahiki ★★★ (www.molokaievents.com) is another not-to-miss event. Islanders celebrate the rainy season—a time of peace and prosperity in ancient Hawaii—with traditional crafts, hula, chanting, games, and competitions. All of Molokai gathers for the daylong event, held on a Saturday in January at the Mitchell Pauole Center in Kaunakakai.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.