The sundrenched beachside town of Lahaina, Hawaii is the largest town in West Maui and a hipstorian’s paradise. It was once the capital of the Kingdom of Hawaii and was crisscrossed by freshwater canals, earning it the nickname the “Venice of the Pacific,” until the water was diverted to the sugar and pineapple plantations in the mountains in the mid-nineteenth century. (Oh how I wish I could have seen the town when it was covered in canals). The town was a bustling seaport for whaling ships, missionaries, and immigrants arriving to work the nearby plantations. Today it is a tourism hub– home to flip flop shops, restaurants with ocean views, and historical sites.

Front Street

Lahaina’s main street, Front Street, is lined with buildings dating back to the 1820s that are now home to shops and restaurants. Almost every shop on this street is repurposed in some way. Stop into Tilly Timms for the best souvenir t-shirts in Maui, or grab some cookies from the Honolulu Cookie Company for an afternoon snack or a take-home for your sweet-toothed sweetheart. Grab lunch at Koa’s Grill upstairs or Kimo’s next door for a great ocean view, and make a reservation ahead of time at Fleetwood’s. On the second floor. At sunset. (More on that later).

The Pioneer Inn + Theater

The Pioneer Inn is the oldest hotel in Lahaina, built in 1901. It is still a hotel today, but the shops along the side of the building were once home to the Pioneer Theater, where workers came to see Hollywood films in the early twentieth century.

The Blue Max | Lahaina Pizza Co.

In the 1970s, the plantation era was ending, and Lahaina was making its mark as a tourist destination. Many celebrities discovered the sleepy town, and The Blue Max hosted musicians like Elton John, Linda Ronstadt, Fleetwood Mac, Crosby, Stills + Nash, Eagles, Rolling Stones, etc. It’s now Lahaina Pizza Co. Stop in for a tropical drink and a “Sweet Pig” pizza with pineapple and ham.

Old Lahaina Courthouse

Built in 1859 as a courthouse, jail, and customs house for the whaling and trade ships, the Old Lahaina Courthouse was redone in the Greek Revival Style in 1925. Today it houses the visitor center, a free museum, and art galleries, including a display of community art in the old basement jail cells.

The courthouse is lovely, and a nice stop for some free art and history displays. But probably the best part of the courthouse is out the back door.

Banyan Tree Park

Banyan Tree Park is home to the largest banyan tree in Hawaii. The enormous banyan has been lovingly shading the courthouse courtyard since 1873, when it was planted to commemorate the 50^th anniversary of the first Protestant mission in Lahaina. The tree has 16 trunks that were once branches that touched the ground and took root. It is 60 feet tall and covers a 200-foot area. There is something very magical and comforting about sitting in the shade of the motherly banyan tree. Grab a Dole Whip at Lappert’s Ice Cream next door and spend some time in the shade of Banyan Tree Park.

Cookhouse Theater

Chinese immigrants arrived in the nineteenth century on trading and whaling ships and to work on sugar plantations. They helped build the tunnels and irrigation systems seen from the famous Road to Hana. In the early 1900s, they formed the Wo Hing Society and built a meeting hall on Front Street that still stands and is now a museum. The Cookhouse Theater in the backyard was built for cooking large meals for society functions and now shows films of the island made by Thomas Edison at the turn of the century.

Old Lahaina Store | Fleetwood’s on Front Street

Built in 1916 as a company store and butcher shop selling groceries and goods to Lahaina locals, The Old Lahaina Store was once known as the finest building in Lahaina. It is now home to Fleetwood’s on Front Street (owned by Mick Fleet of Fleetwood Mac fame) and other shops.

If you’re visiting Lahaina, a visit to Fleetwood’s is a must. Call ahead and make a reservation for the second-floor deck at sunset. With the incredibly beautiful West Maui Mountains to your back and the ocean and setting sun in front of you, you’ll have an memorable meal with unique entertainment, including a bagpiper, traditional Hawaiian conch shell blower, and a variety of live bands. Get the pink salted fries and scallop with risotto as an app and choose from their hearty menu like Australian Rack of Lamb or Beef Wellington.

We were lucky enough to get to hear Joe Bachman + The Tailgaters on our last night in Hawaii. (Never thought we’d find a country band in Maui!) You may even be lucky enough to get a performance by Mick Fleetwood himself if he’s in town!

Explore these hipstoricals and 65 historical and cultural sites through the self-guided Ala Hele Mo‘olelo O Lahaina / Lahaina Historic Trail! A trail map can be downloaded at  http://lahainarestoration.org/lahaina-historic-trail

Suggestions for more hipstorical places in Maui? Email me and help me build my archives!