Early October in Hawaii is a fantastic time to visit. The summer tourist crowds disappear, the weather stays beautiful, and ticket prices usually dive lower compared to the peak season. While you won’t find corn mazes and colorful foliage in this tropical paradise, Hawaii offers its own spin on the autumn season offering year-round beaches and hiking trails. Plan a Columbus Day weekend escape by booking one of numerous Hawaii vacation rentals. Take a look at the most breathtaking cities in Hawaii.
Fall brings out many festivals in Hawaii. Experience this tradition during a weekend in Kahului, on Maui, which puts you within a short drive of the annual Maui Fair. Bring the family to taste local food, watch the Baby of the Year Contest, and cheer on competitors in the Maui Fair Pie Competition. The rest of the weekend, enjoy the casual vibe in town as you visit the Alexander and Baldwin Sugar Museum and its nearby sugar factory, shop at the Maui Swap Meet to find great bargains, and explore the Maui Tropical Plantation, a working sugar and pineapple farm.
2. Haleiwa Town
Experience the early part of the legendary North Shore surf season on Oahu with a Columbus Day weekend getaway in the relaxed beach community of Haleiwa Town. In early October, the waves don’t quite reach their massive winter heights, so fall time presents a great time for a beginner lesson. If you’d rather watch, catch a glimpse of the pros at Waimea Bay or the Banzai Pipeline off of Ehukai Beach. Cool off on sunny days with a classic shaved ice, and take a road trip to the Polynesian Cultural Center in Laie for a bit of cultural history of the area thanks to live demonstrations.
Vacation rentals in Hilo put you close to the coolest fall weather in Hawaii on top of Mauna Kea on the Big Island’s north side. The summit of this volcano sits at 14,000 feet above sea level, providing crisp, cold air year round. Bring a jacket for your drive to the top, and visit the Mauna Kea Observatory for an evening of stargazing. Down at sea level, revel in the warm October air with a visit to Rainbow Falls or the Hawaii Tropical Botanical Garden.
Spend a sunny October weekend swimming and paddleboarding from the lava-rock beaches in Kailua-Kona on the Big Island. Start your days with legendary Kona coffee, enjoy snorkeling to catch a glimpse of tropical fish at King Kam Beach, or go shopping at local establishments on Ali’i Drive. The Ironman World Championships traditionally happen in Kailua-Kona the weekend after Columbus Day, so you have a great chance of seeing world-class athletes getting ready for the race at Kailua Pier. The pier itself gives you a chance to rent a boat for a day-long excursion.
Experience Hawaii’s take on classic fall activities with a visit to Waipahu on Oahu. A few miles away, Aloun Farms celebrates the season with an annual Pumpkin Festival. Visit the farm to take an educational tour and walk through its pumpkin patch. Go for a horseback ride, visit the animals in the petting zoo, or watch live music on the Plantation Stage.
Recreate the classic autumn corn maze experience during your Columbus Day trip to Wahiawa, Oahu. Just outside of town, the Dole Plantation contains the massive Pineapple Garden Maze for family fun. Lace up your hiking shoes and try to find your way through the maze, which covers 3 acres and contains 2.5 miles of walking paths. After your adventure, head back to town to enjoy the fall weather at the Wahiawa Botanical Garden to see fantastic tropical flowers, or the Leilehua Golf Course with amazing mountain views.
Get off the beaten path in Kaupo, a remote area of Maui. Early October, alongside the pleasant weather, represents the perfect time to get outdoors. Rent a four-wheel drive vehicle and explore the dirt roads out of town, or head over to Haleakala National Park and hike the Pipiwai Trail through a spectacular bamboo forest. Along the way, check out the majestic Waimoku Falls with its rainbow mists and sheer rock face.
Check out two of Hawaii’s most exciting beaches without competing for space with summer tourists from your vacation rental in Naalehu on Big Island. To the south, hike along the shoreline to reach Papakolea Beach, more commonly known as Green Sand Beach, to sunbathe on the bizarre green sand. To the north, the spectacular Punalu’u Black Sand Beach shows off with its rich black sand and frequent turtle sightings. Send some mail to your rental home from the southernmost post office in the United States Postal Service.
Vacation rentals in Waimea place you within a short drive of the mind-boggling Na Pali Coast on Kauai’s western shore. If you’re feeling active, drive to Koke’e State Park and hop on the Awa’awapuhi Trail to view its towering vistas of the Pacific. In October, the low crowd levels mean you have the panoramic views all to yourself. For a more relaxing adventure, book a boat tour of the coast with companies like Capt. Andy’s or Makana Charters.
Get a taste of fall at Waimanalo Country Farms in Waimanalo on Oahu. Each October, the farm features hundreds of brilliant orange pumpkins as part of the Pumpkin Patch Event. Visit on the weekend, as weekdays are reserved for school groups. After a day on the farm, enjoy the fall sunshine on the beautiful sands of Bellows Field Beach Park or Sherwood Beach.
Enjoy Hawaii’s biggest city in Oahu without the holiday crowds on a weekend in Honolulu. Columbus Day is relatively quiet in the city, so you can visit Waikiki Beach, Diamond Head State Monument, and the USS Arizona Memorial at Pearl Harbor in relative peace. Take advantage of the warm weather to hike the Makapu’u Point Lighthouse Trail or relax on Kailua Beach. During the occasional early October rain shower, head for the Ala Moana Center for the city’s best shopping.
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