Travel Portland's tourism campaigns have featured the nation's largest free-standing cuckoo clock, stop motion and other animated videos, and Mr. Dude, a Bigfoot-like mascot to market the city to Japanese tourists.

In 1999, the organization proposed an analysis of ground transportation services to reduce conflict during a time of "brutal competition among cabs, town cars, shuttles and limos for fares at the airport".

[6][7] In September 2001, the computer worm known as Nimda disabled POVA's servers for less than 48 hours, temporarily limiting employee access to email and stored files.

The Oregonian reported, "large plastic sheets are tacked to the ceiling below the skylights and covering tourist brochures in a display case at the [POVA] counter.

[26] In 1985, POVA collaborated with the Port of Portland and tourism officials in Oregon and Washington to bring Japanese tourists to the Pacific Northwest.

[37] Fareless Square was also expanded to cover the Lloyd District, Oregon Convention Center (OCC), and Rose Quarter, as part of an agreement between the city, Multnomah County, Metro, the Tri-County Lodging Association, national rental car companies, and POVA.

[40] Mayor Vera Katz announced the formation of the Pacific Gateway Alliance in 2001; the agreement between the cities and ports of Portland and Vancouver, Washington, as well as POVA and the Portland Development Commission (PDC), was created to "promote our companies to the world as never before, with the goal of creating new markets for exports, tourism and business investment".

Katz said the alliance would "support local efforts such as deepening the Columbia River navigation channel while complementing our environmental clean-up in the Portland harbor".

In 2001, The Oregonian said POVA's annual "Big Deal" campaign historically promoted Portland tourism in California, Idaho, Oregon, and Washington for October through May.

POVA's promotional video featured Allow Me, John Seward Johnson II's 1983 bronze sculpture at Pioneer Courthouse Square of a man holding an umbrella, and the organization used business cards depicting raindrops.

[45] In 2005, POVA was among sponsors of a fundraiser organized by the Portland Business Alliance to help mayor Tom Potter and commissioner Sam Adams pay off political campaign debts.

[49][50] In 2006, The Oregonian said POVA and Gordon Sondland of Aspen Investments of Portland "pushed for a minimum of 400 rooms, which would require less public subsidy".

[51] POVA, U.S. Bank, and other organizations sponsored Portland; The View from Here, a pictorial biography by photographer Robert Reynolds, in 2006.

[52] In 2007, the newspaper said POVA "dangles the story" of Portland's Shanghai tunnels "as a lure to out-of-towners"[53] and "concentrates on selling not only the city, but also its proximity to adventure".

According to The Oregonian, the delegation "captured the attention of New York media" and Katz and others were scheduled to appear on the television programs Today and NBC Nightly News.

[71] POVA representatives were also part of a 50-member delegation to travel to Sapporo, one of Portland's sister cities, with Potter in early 2005.

[73] In 2022, POVA's "Cool Summer Deals" program offered discounts on attractions, restaurants, shopping and transportation to visitors who made reservations at 28 participating hotels,[74] and December's "Portland Big Deal" campaign saw approximately 30 local hotels offer special holiday package, some of which included gift wrapping, tickets to the arts, wine tastings, and mistletoe left on pillows.

[86] Travel Portland, the PDC, and mayor Adams were credited for recruiting the North American Handmade Bicycle Show, which was held at the OCC in February 2008.

In 2003, the organization launched an LGBTQ-focused brochure, which was updated in 2005 to highlight "new gay friendly clubs and culture -- along with the beautiful scenery, vibrant culinary scene and tax-free shopping".

[91][92] The "blue furry, Sasquatch-like creature"[93] was created in 2016 as part of a campaign called the "World of Odnarotoop", a name derived from the Japanese pronunciation of Portland, spelled backwards.

Portland City Council approved $100 million in bonds funded by a 2.5 percent tax on hotel and car rentals.

[103] The Oregonian credited Katz for uniting Metro, Multnomah County, POVA, and TriMet to make the Visitor Development Initiative possible.

[107] POVA and RACC published a new walking tour brochure and map featuring approximately 100 public artworks in the Portland metropolitan area in 2005.

The project displayed a series of posters for films and television shows shot in Oregon, over a 160-foot (49 m) mural by Darren Cools.

[110] The organization funded a mural visible from Martin Luther King Jr. Boulevard in southeast Portland with the text "support working artists" in 2023.

The project by the Portland Street Art Alliance and artist Hayden Senter included four bridge column murals in the Central Eastside.

Two of the columns commemorate the Pearl District's Lovejoy Columns, one honors the Portland Rose Festival's dragon boat races, and another is about the Ground Score Association, which the Portland Tribune described as the city's "democratic worker association of dumpster divers, canners and waste pickers".

In 2003, The Oregonian said POVA had an advertisement a few years prior that "obliquely mentioned that despite Portland's relative small size, one of its many attributes included access to 'the world's biggest shoe company'.

"[112] POVA asked Adidas and Nike to sponsor fun runs during annual trade shows for national engineering and science associations.

POVA has also helped organize tours of the Nike World Headquarters "for out-of-town VIPs", including officials from Bologna (one of Portland's sister cities) in June 2003.