In a nutshell: “Upcountry” is a term which describes not only a way of life, but much of the area on the Haleakala side of Maui away from the shoreline. The largest towns Upcountry are Pukalani, Makawao, Kula and Haiku. Although Upcountry is mostly rural, agricultural and residential, Upcountry Maui also offers quite a bit for visitors too.
Minuses: No beaches, and far less tourism oriented.
Sound-bite: “Excuse me ma’am, how do I get back to the down-country?”
“Upcountry” is as much a lifestyle as it is a place. Many people who live Upcountry consider themselves to be quite different from those fancy “city-slickers” who live in paces like Kahului, Wailuku, Kihei or West Maui. Take the “up” off and you have the closest translation of what this term would mean on the mainland: “Country” (with a capital C!) There are Upcountry bumper stickers that proudly proclaim the owner’s mindset, and depending on who you ask, many folks have an opinion on who/what/where is qualified to be considered worthy of that label.
Back to the geography: like all the geographic regions in Maui there are no precisely defined boundaries to Upcountry (more accurately: especially Upcountry!) For example, depending on who you ask, Upcountry can start in, just above, or well above Paia Town. Parts of Paia could be any or all of: “Upcountry”, “Central Maui”, “Road to Hana” and even “North Shore.” One thing is in definite agreement: Upcountry has no water sports
Upcountry Maui has several thoroughfares, but the Haleakala Highway (Hwy 37), Maui’s biggest highway, will be the entry route into Upcountry Maui for most. Other primary roads are Baldwin Avenue (Hwy 390) which heads from Paia up to Makawao; Makawao Avenue (west Hwy 365), which connects Makawao to the Haleakala Highway; Kaupakalua Road (east Hwy 365) connects Makawao to Haiku and the start of twisty “Road to Hana” section of Hana Highway (mile marker 0 of Hwy 360.)
Upcountry it is especially important to take GPS and online maps (including Google Maps) with a grain of salt. Be aware that there are many private, gated, nonexistent, cane and/or 4WD roads that show on GPS as public roads. Ignore maps that connect Upcountry to South Maui. No public roads exist to connect these areas.
For more specific information on Upcountry Maui, browse the Upcountry Maui category.