10 Most Charming Town Squares In Hawaii
Hawaii is known for its natural wonders, but its small towns also hide gems of history, culture, and community. Many of these towns have quaint squares or central gathering spots where locals and visitors alike enjoy markets, live music, and laid-back strolls. From historic plantation towns to seaside villages framed by palms, these squares serve as cultural anchors that showcase Hawaii’s unique blend of traditions. Here are ten of the most charming town squares in Hawaii, each worth a stop for shopping, dining, and exploration.
Lahaina, Maui
At the heart of Lahaina lies its beloved town square, shaded by the enormous banyan tree that has grown into a natural canopy covering nearly an acre. Locals and visitors gather beneath its branches for craft fairs, art shows, and live music, making Banyan Court Park both a landmark and a living community hub. Just across the way, the Old Lahaina Courthouse offers a deep dive into Maui’s layered history, showcasing exhibits on whaling, missionary influence, and plantation life. The square opens onto Front Street, where galleries such as Lahaina Galleries, the longest-running family-owned gallery of the state, feature Hawaiian landscapes and Polynesian carvings. Food lovers can enjoy Star Noodle for house-made ramen and Asian-inspired dishes like delicious pork belly steamed buns. As night falls, the square comes alive with outdoor performances, from hula shows to live music, turning the historic area into a vibrant cultural stage that embodies Maui’s history, art, and aloha spirit.
Hilo, Big Island
Hilo’s downtown square sits amid historic storefronts that date back over a century, offering visitors a glimpse of island heritage. Every Wednesday and Saturday, the Hilo Farmers Market fills the square with tropical fruits, fresh flowers, and handmade crafts, including locally grown papayas and Kona coffee. History enthusiasts can explore the Pacific Tsunami Museum, which recounts the island’s seismic past through interactive exhibits and personal narratives. The square also boasts East Hawaii Cultural Center, where rotating art exhibits and Polynesian performances showcase local talent. Foodies will appreciate stops at Ken’s House of Pancakes, serving traditional Hawaiian breakfast favorites all day, like specialty mahi-mahi sandwiches and loco mocos for a daytime fare. A short walk takes visitors to the Wailoa River State Recreation Area, with shaded paths, koi ponds, and river views perfect for a leisurely stroll. Hilo’s square seamlessly combines history, art, food, and community warmth, giving visitors a fully immersive Big Island experience.
Waimea, Big Island
Waimea’s town square captures the essence of Hawaii’s paniolo, or cowboy, heritage, blending ranch life with community charm. Visitors can watch demonstrations at Parker Ranch Headquarters, one of the largest U.S. cattle ranches, or explore the ranching museum to learn about the lives of Hawaiian cowboys. The square hosts a lively farmers' market, featuring fresh produce, baked goods, and handmade crafts that reflect the region’s agricultural bounty. Art lovers will enjoy The Gallery of Great Things, where local artists showcase crafts, paintings, and sculptures inspired by island landscapes. Food stops include Village Burger for grass-fed beef burgers, which are ranked among the top ten best burger establishments nationwide, with exquisite platters of red veal or island-style wagyu burgers. The town’s shops, like Mea Aloha Gift Shop, sell unique handcrafted jewelry, cute merchandise, and kids' books. Surrounded by rolling green hills, Waimea’s square offers history, cuisine, art, and ranching culture in one charming, walkable hub.
Paia, Maui
Paia’s square is a colorful hub where surf culture, art, and island charm meet. You can start your day at Story Maui with a fresh island fruit bowl and a thin mint matcha latte paired with a veggie-stacked bagel. Food lovers will not want to miss a lunch at Paia Fish Market for grilled seafood or the house-favorite blackened sashimi. On Friday evenings, the square hosts street performers and live music, filling the streets with vibrant energy. Art enthusiasts can explore galleries such as Pueo Gallery to view an intimate assortment of landscape paintings and island-home inspired display objects and glass ornaments of sea creatures that make wonderful gifts. Nature is just steps away at Baldwin Beach Park, where golden sands and gentle waves invite swimming or sunbathing. Paia’s town square is small yet full of character, blending surf, art, food, and coastal beauty into an authentic Maui experience that’s lively, creative, and unmistakably Hawaiian.
Lanai City, Lanai
Lanai City revolves around Dole Park, a shaded square surrounded by Norfolk pines, which serves as the community’s gathering spot for markets, picnics, and festivals. The Lanai Farmers Market showcases local produce, tropical fruits, and handmade crafts, offering a taste of the island’s legacy every Saturday. History buffs can explore the Lanai Culture & Heritage Center, which details the island’s pineapple plantation era and cultural heritage. Blue Ginger Café serves fresh pastries, coffee, and light meals made with locally sourced ingredients, spanning from Saimin noodles to Lanai omelets. Visitors can stroll around the square, appreciating the town’s plantation-era architecture and panoramic mountain views. For outdoor fun, you can also head to the Manele Gold Course, which is remarkably prestigious and great for experiencing spectacular views. Lanai City’s town square exudes a relaxed, welcoming atmosphere where history, food, and community life converge, giving travelers a peaceful yet culturally rich glimpse into island life on one of Hawaii’s quieter gems.
Hanalei, Kauai
Hanalei’s town square is a scenic hub framed by emerald mountains and just minutes from the bay. Visitors can browse art galleries like Hanalei Art Gallery, which displays vibrant local paintings and Polynesian-inspired crafts. The space also hosts studio tours and paint party experiences for special celebrations. Foodies can stop at Hanalei Bread Company for fresh pastries and sandwiches, an open-air coffee shop that is always buzzing with crowds and offering pre-packed beach picnic fares. Waiʻoli Huiʻia Church, with its green steeple, exudes both charm and history in the town center. On weekends, the square comes alive with farmers' markets and live music, offering tropical produce, flowers, and handmade crafts alongside performances from local musicians. Shops like Hula Moon Gifts sell handcrafted seashell-inspired souvenirs that reflect Kauai’s creative spirit. With its combination of natural beauty, artisan culture, and culinary treats, Hanalei’s town square captures the charm, artistry, and aloha of North Kauai in one lively setting.
Kailua, Oahu
Kailua’s town square offers a small-town feel close to Oahu’s urban centers. You will come across boutiques like Lanikai Bath & Body, which sells handmade soaps, lotions, and Hawaiian-inspired gifts. There, you can find products made from pure essential oils and blends of fragrances free from intoxicating aromas. The Kailua Farmers Market brings fresh tropical fruits, flowers, and prepared foods to the square on weekends, creating a lively gathering spot. Outdoor lovers can rent kayaks or bicycles to explore Kailua Beach Park, just a short ride from the square. Cafés such as Boots & Kimo’s Homestyle Kitchen offer macadamia nut pancakes and Hawaiian breakfast favorites, while Over Easy serves creative brunch dishes using local ingredients such as the Kalua Pig Hash or Coconut Shrimp Burger with a side of fresh tomato bloody mary. Live music events and occasional community festivals further enliven the square. Kailua’s town square combines shopping, food, and outdoor activities in a walkable, vibrant setting, providing visitors with an authentic and relaxing experience that captures the spirit of Oahu’s windward coast.
Makawao, Maui
Makawao’s town square blends paniolo heritage with an artsy Upcountry flair, creating a unique hub that reflects Maui’s history and creative spirit. Check out Viewpoints Gallery, which showcases paintings, ceramics, and glasswork inspired by the island’s landscapes, often crafted by resident artists who live and work in the community. Much of their work highlights the legacy and tradition of Hawaiian ancestors. Food lovers can indulge at Komoda Store & Bakery, famous for its fresh malasadas, sweet pastries, and classic Hawaiian treats that draw locals and tourists alike. It was established by a Japanese Plantation worker in the early 19000s and continues to provide the same fresh goods today. The square frequently hosts First Friday art walks, bringing street performers, live music, and food vendors together in a lively celebration of local talent. Nearby ranches allow visitors to learn about traditional ranching practices and experience the island’s rural lifestyle. Makawao’s square is a vibrant intersection of art, history, and culinary delight, offering a full Upcountry experience in one charming and walkable hub.
Hawi, Big Island
Hawi’s quaint town square is a colorful mix of history, artistry, and small-town aloha, set against the lush backdrop of North Kohala’s rolling hills. The local Gallery at Bamboo features wood carvings, paintings, and jewelry handcrafted by local artisans who capture the spirit of Hawaii in every piece. As for the perfect coffee spot, Kohala Coffee Mill Café is where you can enjoy freshly brewed Kona coffee, pastries, and a warm, inviting atmosphere perfect for a morning pause. Near the square, find your way to the waterfalls for a swim at the Kohala Waterfalls Adventure or bring a friend to race on the Kohala Zipline. There are plenty of small and quirky shops to pick from, whether you’re after fair-trade jewelry or unique sandals. As Hawi Turns is a must-stop. With its combination of art, history, cafés, and community events, Hawi’s square captures the essence of small-town Hawaiian life, making it an unforgettable stop for travelers seeking culture, cuisine, and charm.
Kapaa, Kauai
Kapaa’s Old Town Square is a vibrant blend of local culture, art, and community spirit. Start off with Pono Market, a local institution known for its delicious plate lunches and poke bowls, offering a taste of authentic Hawaiian cuisine. Just a short walk away, Java Kai serves up freshly brewed coffee and a variety of baked goods, including gluten-free muffins and vegan brownies, making it a popular stop. On the first Saturday of each month, the town comes alive with the First Saturday Art Walk, where over 100 artisans line the streets selling pottery, paintings, photography, woodcarvings, and shell jewelry. The event also features a wide variety of food booths and live entertainment, creating a festive atmosphere that showcases the island's artistic talent and culinary delights. For outdoor enthusiasts, the Ke Ala Hele Makalae, or “The Path that Goes by Coast,” coastal path offers a scenic route for walking and biking, providing stunning ocean views just minutes from the square. With its mix of local flavors, artistic expressions, and natural beauty, Kapaa’s town square offers a truly authentic Hawaiian experience.
Hawaii’s small-town squares reveal a side of the islands beyond beaches and resorts, combining history, culture, and local life. From Lahaina’s banyan-shaded park to Kapaa’s artistic streets, each square offers unique shops, galleries, eateries, and outdoor experiences that showcase the islands’ diversity. Visitors can enjoy handmade crafts, locally sourced cuisine, live performances, and historic landmarks, all while soaking in the aloha spirit. Exploring these charming town centers allows travelers to slow down, engage with local communities, and experience authentic Hawaii in settings that are welcoming, vibrant, and unforgettable.
