Road Trips near Indianapolis

Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.

How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

See our road trips below, or check out our quiz and trip map to help find your perfect adventure.

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! The recipient can then choose a surprise trip that suits them!
  • BEST DONE SPRING-FALL
    Lakeshore Views & Brews

    Lakeshore Views & Brews

    $39 CAD
    Stroll along a breathtaking boardwalk, dip your does in the cool water, sip craft drinks in unique destinations, and take lots of funky photos! This road trip will certainly let you unwind from the hustle and bustle of the city.
    • Kid-Friendly
    • Accessible
    Can depart from: Chicago Area
  • FOR COUNTRYSIDE DRIVES
    Cozy Country Charm

    Cozy Country Charm

    $39 CAD
    The perfect blend of rustic allure, cute small towns, cozy cafes, and farmstead feelings makes this a fantastic road trip for those looking to slow down and appreciate the little moments.
    • Kid-Friendly
    • Accessible
    Can depart from: Indianapolis Area
  • EXPLORE AN ICONIC AREA
    Countless Covered Bridges

    Countless Covered Bridges

    $39 CAD
    Take a leisurely drive through the idyllic countryside, hopping from one quaint covered bridge to another. We've sprinkled in a few local eateries and easy trails to give your camera a break! 
    • Dog-Friendly
    • Kid-Friendly
    Can depart from: Indianapolis Area
View all