11 of the Best Trails, Tours, and Passports in 2023

One of the fastest growing trends influencing local hospitality industries are check-in Challenges, AKA: trails, tours, and passports.

By gamifying and incentivizing travelers to visit destinations based on season, trend, or niche, destinations can leverage Challenges to create one-of-a-kind travel experiences, activate untapped markets, and see results with valuable insights and economic impact.

New to Challenges? Here’s the Scoop:

Challenges highlight attractions within a destination (neighborhood, city, state, country – the possibilities are endless) through gamified check-ins. Visitors follow a curated trail, digitally “check-in” at each attraction, and are rewarded with virtual badges – or passport stamps– and super fun prizes. 

With a heavy emphasis on engaging leaderboards, social shares, and redeemable rewards, Challenges are inherently viral and offer destinations unique opportunities to market to both local and broad audiences. 

Best Examples of Challenge Marketing in 2023

In this article, we’ve rounded up our top 10 favorite Destination Marketing Organizations (DMOs) who are using Challenges to market their destinations. What’s more, we’ll tell you why each Challenge works so that you can level up your destination’s market game with Challenges in 2023.  

Before diving into our list, let’s take a closer look at how destinations benefit from leveraging Challenges.

How Do Destinations Benefit From Hosting Challenges? 

We’ve already described the appeal of Challenges for tourists. But if you’re marketing a destination, whether it be a city, state, event, or even a national park — you’re going to want to get in on the action. Here’s how destinations benefit from offering tours and passports to the public.


Challenges activate, engage, and mobilize locals and tourists to visit your destination and its best attractions. In addition to highlighting the amazing experiences available at your destination, visitors also have the incentive of free rewards and prizes to look forward to as they check-in around town, share their status on social, and track their progress on the leaderboard. 


Challenges offer destinations a unique opportunity to educate visitors about what they have to offer. Challenges help tourists become more knowledgeable about things to do in and around a region and activate locals to explore their hometown with fresh eyes. This not only creates a holistic experience for travelers, but also helps build traction for businesses in an area while stimulating economic growth and public interest.


Let’s not forget one of the biggest drivers of business in today’s world — marketability. As participants engage with your destination, they take photos and videos, share and tag places within your destination, and drive organic growth. User Generated Content (UGC), or content created organically by your visitor, has been shown to be more effective in driving conversions than traditional content. Challenges can be an effective tool for driving UGC from your most engaged visitors. Challenge marketing tools prompt participants to share a photo or video of the business they visit as part of the completion criteria for the Challenge. These assets can then be shared across social channels.


One of the biggest perks of Challenge marketing is that it provides feedback and data from participants. Many of today’s tools for Check-in Challenges offer visitors the ability to leave tips or comments about the attraction. This provides incredibly valuable insights for both the DMO and the businesses which allows them to make necessary changes based on feedback.

Economic Impact

Curated tours and experiences create a network of local offerings for visitors to flock to. This helps all businesses grow and drives sales for the community. It is thus highly beneficial for the economy of the city or town where the challenge tour is located.

Our Favorite Challenges (Tours, Trails and Passports) for 2023

Now that we know why Challenges are awesome for everyone involved, let’s highlight 10 destinations who are mastering the art of Challenge marketing in 2023:

1. Discover Black Cville

Charlottesville, Virginia

Black Cville invites visitors to celebrate African-American culture, stories, and traditions in Virginia. Set in the flourishing and warm neighborhood of Charlottesville, travelers can sign up for tastings at local wineries, tour heritage centers, shop for organic and handmade cosmetics, sample European-style bread and pastries, and more.

Best enjoyed during the fall, the Discover Black Cville passport encourages visitors to immerse themselves in the community’s history as well as the masterpieces of its local artisans. Tourists who check-in at five Black-owned and operated businesses can redeem an exclusive Black Cville hat.

Why We Love It

  • Evergreen: As the city and community grows, more and more Black-owned businesses pop-up, which means new experiences and Challenge-goers.
  • Timely: It’s the perfect way to celebrate special dates and holidays like Black Business Month and Juneteenth (which commemorates the emancipation of enslaved African Americans).

2. KC Parade of Hearts

Kansas City, Missouri

Those looking to immerse themselves in Kansas City’s thriving art scene won’t be disappointed with the KC Parade of Hearts. The Challenge is more than an art exhibition — it’s an experience. Skilled and talented local artists from all over come together to support non-profit organizations by making magnificently designed hearts that are placed all around the city.

Each year from March to June, the 5 x 5-foot heart-shaped artwork of over a hundred local artists will be displayed around the city for people to find. Each heart-shaped sculpture features a unique design that gives viewers a peek at the artist’s story and inspiration.

Why We Love It

  • Timebound: The hearts will be paraded in May 2023. From June to July, they’ll be moved to different locations before being auctioned off.
  • Social/Viral: The Parade of Hearts has become an event that embodies the pride, solidarity, and sense of community that’s shared by all Kansas City residents. It has an active Instagram account that encourages local shares and where various local businesses are tagged.

3. Nebraska Holiday Passport

Lincoln, Nebraska

Make the most out of Christmas in Nebraska by picking up a Nebraska Holiday Passport. This mini-passport invites its holders to explore 20 unique holiday stores and experiences. Valid from November 19 to January 1, 2023, the Nebraska Holiday Passport is one’s ticket to charming cafes, amazing eateries, cozy lodges, and beautiful Christmas-themed attractions. Participants can enjoy discounts on food, drinks, and activities where they can win prizes like lottery coupons and a Champion Holiday Tree ornament.

Why We Love It

  • Seasonal: Christmas is the biggest American holiday of the year, and the Nebraska Holiday Passport capitalizes on this festive time. As we come closer to the year’s end, passport holders can enjoy a sweet and sentimental experience while indulging in limited-edition treats and incentives.

4. Scooped: An Ice Cream Trail

Pittsburgh, Pennsylvania

Pennsylvania’s Scooped Ice Cream Trail is just as exciting as it sounds. After all, who wouldn’t love tasting delicious, artisanal ice cream all day long? Even better, patrons get rewarded for their sweet tooth. After 10 check-ins, participants who’ve been following Scooped’s ice cream trail get a free Scooped Ice Cream Scooper. 

This unique and tasty experience will surely delight all the dessert lovers out there. They get to visit dairy farms and ice cream shops while sampling one delicious flavor after another!

Why We Love It

  • Niche: The Scooped Ice Cream Trail offers experiences that are specific to the Pennsylvania region while promoting local dairies and creameries.
  • Quirky: Ice cream lovers can indulge their taste buds and sweet tooths by exploring all the weird and wild ice cream flavors this trail has in store for them.

5. Sonoma Wine Passport

Sonoma, California

Since Sonoma is known for its excellent wineries and vineyards, getting the Sonoma Wine Passport means indulging in rich and robust wines, cheese platters, and delicious food. Even better, the Sonoma Wine Passport offers amazing deals and discounts (such as 5% to 10% discounts on products) from wineries and vineyards that are on the list.

Once you receive a passport, members have access to all vineyards and wineries in the Sonoma area until the end of the year. After all, there’s nothing that a good glass of wine (or two!) can’t fix.

Why We Love It

  • Evergreen: This is a dynamic passport that provides holders a growing list of places they can visit each and every year.
  • Niche: The venues on this list are top-tier and recognized worldwide for the quality of their products and ingredients. If you’re a wine lover, tasting it at the source is a once-in-a-lifetime experience.

6. Passport to Your National Parks

Yosemite National Park, California

Passport to Your National Parks is designed for avid hikers who love spending time outdoors. Since 1986, national park lovers have relied on the brilliant initiative by Eastern National. Their best-selling guidebook, Passport To Your National Parks, lets readers collect ink stamps for each of their visits.

Once purchasing a passport, participants can take their booklet to any national park visitor center or park store and get a free ink stamp with their visit date and location. 

Passport-themed apparel and accessories are also available for visitors to show off their love for America’s national parks. The best part is all proceeds from the program go toward national parks’ ongoing education and preservation efforts.

Why We Love It

  • Evergreen: There are so many parks that can be visited year-round.
  • Nationwide: Instead of focusing on an audience that’s limited to towns or states, this passport appeals to park-goers across the country. 
  • Bucket list: Many national parks are huge and can’t be toured in just a few days. Visitors are bound to come back for repeat visits.

7. Milwaukee Cheese Curd Pass

Milwaukee, Wisconsin

Curd nerds and cheese lovers, unite! This is the tempting invitation participants get from the Milwaukee Cheese Curd Pass. Holders of the Curd Pass sign up to follow a digital curd trail that includes burger joints, breweries, bars, and all manner of dining establishments that offer their favorite fried and creamy curd treats. They can also use their passes to get discounts on some of their favorite curds! If patrons check-in at all the locations under the pass by December 31, 2022, they’ll be entered to win a special cheese curd gift pack and earn the distinction of being a true-blue curd connoisseur.

The Milwaukee Cheese Curd Pass is valid until May 1, 2023, and can be accessed exclusively through smartphones. The pass is received as a text and email so there are no apps that require installation. This is a fantastic way to get to know the Milwaukee neighborhood with your taste buds while supporting small businesses and dairies.

Why We Love It

  • Social: The catchiness of the phrase “curd nerd” encourages social shares and tags local businesses around the region
  • Buzz-worthy: When was the last time you heard of a trail just for curds?

8. Vermont Brewers Association

Montpelier, Vermont

For tourists who love a pint, the Brewery Challenge from the Vermont Brewers Association is their perfect match. To accept the Vermont Brewery Passport Challenge, all interested participants have to do is download an app on iStore or Google Play. Alternatively, they can also pick up official passports at participating breweries and pubs.

Once they’ve secured their passport, visitors can immediately start touring Vermont’s most incredible brewpubs and breweries while collecting stamps as they go. Passport holders are also entitled to discounts and other exciting offers such as free t-shirts.

Why We Love It

  • Evergreen: Beer lovers don’t have to follow any fixed schedules. They can visit as many or as few breweries as they want according to their convenience.
  • Bucket list: Tracking down the perfect craft beer is easier and more fulfilling with a passport that lets holders record their visits. When they find a beer they love, it will be easier for them to revisit the same pub.

9. NY City Sights Pass

New York, New York

Ah, the big apple. Almost everyone dreams of touring the city that never sleeps, but it can be astronomically expensive to see all the noteworthy sites — not to mention difficult to identify all of them. With over 150 attractions and offers, the NY City Sights Pass can be the perfect companion for those who want to make the most out of their big city experience.

New York’s City Sights Pass offers flexible pricing, depending on how many places you want to visit per day and how many days you’re planning to spend in NYC. Tourists can save up to 70% on attractions if they get the Sightseeing Pass which includes entry to 4 observation decks, NY Aquarium, Bronx Zoo, Central Park among others. Upon purchase, holders have 12 months to activate their passes. From observation decks to museums to popular local and international cuisine — this pass covers it all.

Why We Love It

  • Timebound: Participants can choose how many days they want to use the pass and how many attractions they want to visit per day.
  • Deals: The New York Sightseeing Pass lets holders enjoy deep discounts and ticket-free entries to some of the city’s biggest tourist attractions.

10. Greenville, SC Taco Trail

Greenville, South Carolina

Time for a taco trail? Yes, you read that right. The Greenville Taco Trail in South Carolina offers prizes in return for eating delicious, local tacos.

Visitors can choose from 4, 8, and 11 taco trails to satisfy their ultimate taco cravings. Participants also get a chance to win the grand prize: 2 VIP tickets to the Tacos n’ Tequila Fiesta that’s happening in 2023. After visiting each taco stop, participants can get their passports stamped and get free baseball caps and tumblers.

Why We Love It

  • Niche: Tacos aren’t just a food. They’re a lifestyle. From taco memes to taco Tuesdays, this trail attracts bucket list taco lovers from around the world. 
  • Buzz-worthy: Unsurprisingly, this trail made national news with notable features in Forbes and Today.com. 

11. Tech History Trail

Los Altos, California

Ever wonder where Jobs and Wozniak built the first Apple computer? Or where Sergei Brin and Larry Page wrote the first lines of code that would become Google? On this Tech History Trail, you’ll follow the paths of some of the most iconic tech companies in the world, from their garage startup roots to the utopian mega-campuses they are today.

Powered by Seeker, trail participants will check-in at 12 different tech stops in and around Los Altos, California. With each check-in, visitors will track their progress on a responsive, location-aware map. Tech enthusiasts who visit all 12 stops will be awarded Seeker’s Tech History badge.

Why We Love It 

  • Evergreen: There’s no start or end time, here! Participants can take their time with the trail and rack up badges over a long period of time. 
  • Niche: Explore Los Altos’ Tech History Trail offers experiences that are specific to the region (Silicon Valley).

Launch Your Own Challenge With Seeker

Feeling inspired yet? Check-in Challenges are a great way to attract new visitors and activate locals to experience their communities in new ways. From taco trails to public art tours, the possibilities are endless and faster than you may think to get started. Seeker’s turn-key platform makes it easy to launch mobile-friendly Check-in Challenges that drive engagement, UGC and social conversations. Ready to gamify your destination? Schedule a demo with Seeker

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