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Main Street destinations to visit this summer

June 23, 2021
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As Main Street staff members, we are often asked to recommend Wisconsin destinations that are unique, fun and exciting.

Let’s face it: We believe that all Main Street communities have something great to offer. But this month, we’d like to highlight our top three downtown destinations for groups seeking more tailored experiences—families, women and history buffs.

There are excellent destinations for all three groups across Wisconsin. This month, we’ll take you on a virtual tour of some Wisconsin Main Street gems. We hope it inspires you to explore new places in our great state this summer. If you’re interested in creating custom itineraries for your community, keep reading.

Choosing just three communities to feature in each category was difficult, but we used the “rule of four” to identify places where a visitor could easily spend four hours or more engaged in activities geared to their interests.

The ability to spend multiple hours at a destination significantly increases the distance that visitors will be willing to travel, so it’s important to provide a vision for an afternoon or daylong outing that meets their needs. Here are three tips for designing a compelling visitor itinerary for your community:

  • Create a curated experience. It’s common for communities to want to highlight the quantity of options available in their community, either out of a belief that listing more businesses will make the district appear more vibrant, or out of fear of offending anyone left off the list. Offering an all-encompassing list can be paralyzing for would-be visitors who are unsure which option is best for them. Creating a curated list of options targeting three high-quality recommended options to a specific audience is a far more successful strategy. A satisfied customer will explore other businesses and return in the future, while one with a negative experience may not.
  • Think in terms of complementary activities for an afternoon, day or weekend. This may require including activities outside of the downtown area in order to extend the visit. It’s understandable you might hesitate to encourage visitors to leave the district, but if your itinerary is well designed with downtown as a home base, including memorable and targeted experiences outside the downtown, it will enhance visitors’ experiences and ensure that they stay long enough to visit other destinations and businesses.
  • Establish package deals. If you have businesses that are especially complimentary or attract similar demographics, encourage them to promote package deals that encourage visitors to visit multiple destinations. Offering “stay-and-play” packages featuring an overnight stay, rental bikes delivered to visitors’ rooms and dinner packages can create a one-click opportunity to capture visitors looking to try something new.

Here are some well-designed examples to use for inspiration:

Visit Madison – Kid Friendly Itinerary Ideas

Itinerary Ideas – 3 Day Getaway Example

Visit Eau Claire – Family Fun Things to Do

Girls Trip to Galena Road Trip Example

Things to Do – Unique Shopping Ideas

Fun Things to Do – Family Destinations Guide

Video Itinerary – Outdoor Adventures Guide

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