Heading north out of Honolulu, the North Shore's inland border is Dole Plantation, in Wahiawa. From the elevated Dole pineapple plantation, Highway 99 offers gorgeous views of the North Shore and its expansive mountain range and coastline. Much of the land that lies between Dole and the ocean shoreline is to this day used for agriculture and accounts for the majority of Oahu’s agricultural production. Local products from the region include tropical fruits, a wide variety of vegetables, coffee, fish, shrimp, meat, breads, oils and lotions.

Taking a straight line down Highway 99, the North Shore is bordered by a spectacular coastline that has had a large hand in defining the modern-day ambiance of the region. Giant winter swells that dominate from November through March have given rise to a thriving surf-driven economy that has earned the North Shore its nickname of surfing’s 'Mecca'. Home to the largest and longest running surf series in the world - the Vans Triple Crown of Surfing, the North Shore's waves have permeated at every level, influencing lifestyle, local art, restaurants and stores, as well as accommodation and visitor cycles.

To the east of Haleiwa, the North Shore region stretches as far as the Polynesian Cultural Center in La'ie, encompassing world famous beaches the likes of Waimea Bay, Pipeline, and Sunset Beach. Points of interest along the way include Waimea Valley, today stewarded by the Audubon Society; Pu'u O Mahuka Heiau - the largest heiau (Hawaiian religious site or temple) on O'ahu; the Turtle Bay Golf Resort and Spa, and Kahuku - the northernmost point of Oahu and site of several shrimp ponds and lunch wagons and the old Kahuku Sugar Mill.

Heading west from Haleiwa, the region is bound by the Waianae mountain range, including Mount Ka'ala - the tallest peak on O'ahu, and Ka'ena Point - the western-most tip of the north-facing shoreline. Between Hale'iwa and Ka'ena lay many white-sand beaches, including the kite-surfing beach of Mokule'ia. Of all the North Shore, this stretch between Ka’ena, Haleiwa and Dole is the closest represenataion of the North Shore of days gone by, with old plantation homes, fieldworker’s camps and farming and ranching activity.

Historic Hale'iwa town is worth a day-trip on its own. As the economic hub of the North Shore, the town was designated a State Historic, Cultural and Scenic District in 1984. Included in America's Main Street program, all new buildings must adhere to a design plan that reflects the Territorial architecture of Hale'iwa's earlier sugar industry period. The town is home to 34 historic buildings featuring plantation architectural styles influenced by the Waialua Sugar Company.

Hale'iwa’s Main Street houses many unique, locally owned businesses that range from boutiques to boat charters, from surf shops to shave ice, as well as a wide variety of restaurants that cater to every taste.

The North Shore also boasts a full slate of activities for the adventurous and sports-minded. These include surf lessons, fishing charters, polo fields, skydiving and glider rides, diving and snorkeling, shark-watching tours, kite-surfing and windsurfing, horseback-riding, hiking, mountain-biking and dirt-biking, and camping.