Woman holding four Guess Where Trips envelopes while on road trip

Midwest

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

Browse all trips

  • Road Trip Gift Card

    Road Trip Gift Card

    $80.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • Last chance!
    View from inside a wooden covered bridge looking out at a tree-lined road leading to a bright sky.

    Bridges & Beauty

    $50 CAD Sale
    Get ready to wind your way through scenic tree-lined roads, cross charming covered bridges, sip at cozy wineries, hike stunning trails, and maybe even get a chill from a ghostly tale or two.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Cleveland Area
  • CYCLE FRIENDLY
    Sunset over a river with trees in the foreground

    A Riverside Ramble

    $50 CAD Sale
    Wander through colorful sculptures, charming boutiques, and local eateries before discovering breathtaking riverside gems that are so photo-worthy, your camera roll is sure to fill up!
    • Accessible
    • Kid-Friendly
    Can depart from: Chicago Area, Milwaukee Area
  • PERFECT FOR MOVIE BUFFS
    A person holding a camera and taking a photo, with a focus on the camera and the person's hand

    Cinema & Scenery

    $65 CAD
    Discover hidden art, channel your inner movie star, indulge in tasty bites, and enjoy a waterside stroll. This captivating adventure offers a perfect blend of creativity, culture, and coastal charm.
    • Kid-Friendly
    • Accessible
    Can depart from: Chicago Area, Milwaukee Area
  • HALLMARK MOVIE VIBES!
    All Things Charming

    All Things Charming

    $65 CAD
    From snow-dusted lakeside views and quaint small-town charm to playful animal encounters and a whimsical museum, this captivating road trip promises unforgettable moments for everyone in your group.
    • Kid-Friendly
    Can depart from: Chicago Area, Milwaukee Area
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $50 CAD Sale
    Step into a day where every stop sends a shiver down your spine. Ghostly whispers in cemeteries, abandoned ruins, and wooded trails full of chilling stories will leave you wondering if any spirits followed you home.
    • Dog-Friendly
    • Accessible
    Can depart from: Chicago Area
  • OUTDOOR WINTER ADVENTURES!
    Falls, Forests & Fables

    Falls, Forests & Fables

    $39.00 CAD
    Sale
    Get ready for a day filled with charm and easy winter adventures. Start in a small town bursting with colorful murals, then take in riverside lookouts, snowy trails, and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring!
    • Dog-Friendly
    • Kid-Friendly
    Can depart from: Chicago Area
  • BEST DONE SPRING-FALL
    A sandy trail leading to the water

    Lakeshore Views & Brews

    $65 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
  • CAN BE DONE IN WINTER
    Cascades & Colors

    Cascades & Colors

    $65 CAD
    Funky, colorful towns filled with local eateries and shops, icy waterfalls that stop you in your tracks, and one of the most unusual gardens we’ve ever seen. You’ll definitely want your camera out for this trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Columbus Area, Cincinnati Area
  • A LEISURELY ROAD TRIP
    Woman hiking in a forest

    Woodland Walks & Wineries

    $65 CAD
    Funky forest finds are on every stop, which are perfect for the outdoor adventurer. Unique wineries, bakeries, and a museum celebrating a man we have a lot to thank for are sprinkled in for the more leisurely road tripper.
    • Kid-Friendly
    Can depart from: Cleveland Area, Toledo Area
  • A COZY WINTER ROAD TRIP!
    A person holding up a sugar-coated doughnut, likely enjoyed as part of the 'A Taste of Amish Country' experience.

    A Taste of Amish Country

    $65 CAD
    Escape to the quiet charm of Amish country for cheese tastings, sweet treats, craft shops, funky museums, and incredible historic photo ops - all set against peaceful countryside scenery.
    • Kid-Friendly
    • Accessible
    Can depart from: Cleveland Area, Columbus Area
  • CAN BE DONE IN WINTER
    A scenic view of a waterfall surrounded by green foliage.

    Waterfall Wanderings

    $65 CAD
    The ultimate waterfall adventure not too far from home! Wander along historic paths, snap photos of four falls, enjoy a glass of local vino and explore a mysterious cave.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Cleveland Area
  • last chance!
    Rivers & Rural Roads

    Rivers & Rural Roads

    $50 CAD Sale
    Riverside roaming strolls, historic highlights, scenic spots for sipping wine or beer, and some of the prettiest rural roads are just a few of the hidden gems you’ll discover on this trip!
    • Kid-Friendly
    Can depart from: Detroit Area, Toledo Area
  • GREAT FOR ACTIVE FAMILIES
    Sweet Sensations

    Sweet Sensations

    $65 CAD
    Between making a furry friend at a farm, enjoying local eateries, walking to quirky ruins in the woods and exploring the sweetest small town, this trip will make all five senses come to life all day!
    • Kid-Friendly
    • Accessible
    Can depart from: Detroit Area, Toledo Area, Windsor Area
  • YEAR-ROUND JOY
    A festive Christmas-themed miniature village display with snow-covered houses and a large Christmas tree in the center.

    Endless Christmas Cheer

    $50 CAD Sale
    This is the perfect trip for anyone who thinks that extra festive feeling should be a year-round experience. Decorations, cozy shops and eateries, and a picture-perfect covered bridge - oh my!
    • Kid-Friendly
    • Accessible
    Can depart from: Detroit Area, Windsor Area, Sarnia Area
  • A LITTLE BIT OF EVERYTHING!
    A box of assorted donuts with different toppings and glazes.

    Treats & Trails

    $65 CAD
    Is there anything better than a leisurely day sipping hot coffee, enjoying tasty treats, and wandering along quiet snow-covered boardwalk trails? We think not!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Windsor Area, Detroit Area, Toledo Area
  • SCENIC ROAD TRIP
    Groves, Gardens & Grapevines

    Groves, Gardens & Grapevines

    $65 CAD
    This incredibly picturesque road trip is full of whimsical gardens, lookout points, wineries, and easy strolls along forest paths. We think it's an area you'll want to come back to time and time again.
    • Kid-Friendly
    Can depart from: Columbus Area, Cleveland Area, Toledo Area
  • Last chance!
    Medieval castle-like stone structure with a clear blue sky in the background.

    Storybook Strolls

    $50 CAD Sale
    A day full of whimsy, wonder and quirky destinations that will make you feel like you're living in a storybook world. This trip is perfect for the whole road trip crew, from families with kids to girlfriend getaways!
    • Kid-Friendly
    Can depart from: Cincinnati Area
  • FOR COUNTRYSIDE DRIVES
    Cozy Country Charm

    Cozy Country Charm

    $65 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
    A red covered bridge crossing a rocky stream, surrounded by green forest.

    Countless Covered Bridges

    $39.00 CAD
    Sale
    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
  • COZY TRIP NEAR THE CITY!
    Elegant Estates & Outdoor Art

    Elegant Estates & Outdoor Art

    $65 CAD
    Just a short drive from Indy, you’ll find a world of elegant estates, whimsical gardens, and colorful outdoor art - all looking a little extra magical when dusted with snow. We’ll share the quirky fun facts and historic moments that make these spots so unique!
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
    Can depart from: Indianapolis Area
  • Best done spring-fall
    A boardwalk leading to a beach with the sun shining brightly in the sky.

    Southern Express

    $65 CAD
    Think cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Windsor Area, Detroit Area, Sarnia Area, London Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

Take the Quiz
Woman on road trip leaning out window

Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!