Woman holding four Guess Where Trips envelopes while on road trip

2025 Inventory Sale

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

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  • RETURNS THIS FALL
    Historic Haunts

    Historic Haunts

    $39 USD
    This haunted history route blends eerie legends and unusual attractions. Visit spots with documented haunted pasts — from towers and ruins to cemeteries — while uncovering the fascinating tales behind them. Please Note: This trip begins in Cambridge and takes place in the same area as Local Markets & Picturesque Towns.
    • Accessible
    • Dog-Friendly
  • RETURNS THIS FALL
    Spooky Sights & Ghostly Tales

    Spooky Sights & Ghostly Tales

    $39 USD
    Explore spooky ruins, abandoned buildings, and haunted mansions tied to eerie legends, with a mix of walkable trails, photo ops, and even a chance to dine in a haunted restaurant. Please note: some parts of this trip take place within the city of Hamilton, travellers may encounter some traffic.
    • Dog-Friendly
    Sale
  • SCENIC ROUTE
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    $39 USD
    This outdoorsy, story-filled road trip blends spooky legends with beautiful scenery along a rural driving route. A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting. Most haunted sites are best enjoyed from the outside, so bring your curiosity and imagination to make the ghost stories come alive.
    • Dog-Friendly
    • Kid-Friendly
    Sale
  • HIDDEN GEMS
    Workers filling up a glasses of beer at a brewery

    Gardens, Trails & Local Ales

    $65 USD
    If you're into hidden gem breweries and easy outdoor adventures that are close to home, then this is the trip for you! We've also sprinkled in a few bakeries to satisfy your sweet tooth, quirky shops, and some local history throughout the day.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • DIGITAL ONLY
    Woman spinning on the beach.

    Waterside Bliss

    Regular price $39.00 USD
    Beach breezes, coastal eats, and charming strolls await on this picturesque day trip. You’ll wander waterfront boardwalks, explore historic homes, and discover secret spots only the locals know - all with a side of sandy serenity and small-town charm.
    • Kid-Friendly
    • Dog-Friendly
  • GREAT YEAR-ROUND TRIP
    A person outdoors holding a camera up to their face, with a body of water and a blurred background.

    Quirky Delights

    $65 USD
    Not too far from home you'll discover a ton of quirky destinations. Think outdoor folk art, funky eats in a small town, hidden gem riverside strolls, and a local alpaca farm.
    • Accessible
    • Kid-Friendly
  • Digital Only
    A person standing on a trail in a forested area

    Old Florida Trail

    $39 USD
    Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare, explore a few outdoor adventures, and fill up your camera roll with quirky photo ops.
    • Kid-Friendly
    Sale
  • PERFECT FOR SUMMER OR FALL
    Boardwalk leading to a beach.

    Coastal Connection

    $39 USD
    From seaside strolls and spooky ruins to cider donuts and historic mansions, this charming coastal road trip is full of surprises. Whether you’re wandering a 17th-century town green, petting goats at a giant book barn, or soaking in saltwater views, you’ll fall in love with Connecticut’s quirkier side.
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
  • GREAT YEAR-ROUND TRIP
    Tree lined road

    A Drive Back in Time

    $65 USD
    A relaxed Atlanta-area road trip through charming small towns, cozy cafés, and quirky photo stops.
    • Accessible
  • BEST SELLER
    Wonder & Whimsy

    Wonder & Whimsy

    $65 USD
    Embark on a day trip where lakeside strolls, whimsical gardens, and charming small-town shops and eateries are just the beginning. Along the way, you'll explore a quirky hotel, a few scenic sights, and even read a haunted tale or two!
    • Kid-Friendly
  • CYCLE FRIENDLY
    Sunset over a river with trees in the foreground

    A Riverside Ramble

    $65 USD
    A scenic Chicago-area road trip with art, boutiques, eateries, and riverside views.
    • Accessible
    • Kid-Friendly
  • GREAT OVERNIGHT TRIP
    Seaside Legends

    Seaside Legends

    $65 USD
    Little local legends are sprinkled throughout your day, telling the story of an iconic area of Florida. Expect picturesque beaches, tasty eats, a historic city, and so much more.
    • Kid-Friendly
    • Dog-Friendly
  • A CLOSE TO HOME ADVENTURE
    Timeless Towns & Scenic Sips

    Timeless Towns & Scenic Sips

    $65 USD
    Brews, bites and a whole lot of history! From small town charm to tasty tipples and one of the most unique (and eerie) trails we've ever found, this road trip has something for everyone.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
  • 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

    $65 USD
    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
  • DOG-FRIENDLY TRIP
    Falls, Forests & Fables

    Falls, Forests & Fables

    $65 USD
    Get ready for a day filled with charm and easy outdoor adventures. Start in a small town bursting with colorful murals, then enjoy riverside lookouts and even some surprising wildlife. This trip is perfect for those who love to stay active while exploring!
    • Dog-Friendly
    • Kid-Friendly
  • GREAT WEEKEND GETAWAY
    Man standing on a road looking up among towering trees

    Forests & Funky Finds

    $65 USD
    This trip is the perfect overnight getaway! As you're driving through the woods, you'll hop between the cutest small towns full of charming shops and eateries.
    • Kid-Friendly
    • Dog-Friendly
  • Last chance!
    View from inside a wooden covered bridge looking out at a tree-lined road leading to a bright sky.

    Bridges & Beauty

    $65 USD
    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
  • Last chance!
    A thematic setup featuring items related to witchcraft and Halloween, including pumpkins, candles, books, and various decorative elements on a table.

    Witchy Wonders

    $65 USD
    This road trip will have you exploring the Salem witch trials, haunted history and a few iconic Hocus Pocus locations. This trip can be done throughout the year. If you're travelling during the month of October some attractions need to be pre-booked as the area gets significantly busier.
    • Accessible
    • Kid-Friendly
  • SPOOKY STORIES
    Eerie Escapes

    Eerie Escapes

    $65 USD
    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
  • EXPLORE AN ICONIC AREA
    A red covered bridge crossing a rocky stream, surrounded by green forest.

    Countless Covered Bridges

    $65 USD
    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
  • LAST CHANCE
    Strange & Spooky Sights

    Strange & Spooky Sights

    $65 USD
    Get ready for a spine-tingling adventure as you explore some of the most haunted and historic spots in the state. Along the way, you'll encounter restaurants and cafes with ghostly legends, strange stories, peculiar museums and haunted objects galore — perfect for anyone who loves a good thrill mixed with quirky charm!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • SCENIC DRIVES
    Wooden bridge overtop of moving river and surrounded by forest trees.

    Valleys, Vistas & Falls

    $65 USD
    Wander through lush forests, meet rooftop goats, enjoy a riverside pint, and chase waterfalls on this Vancouver Island road trip packed with quirky charm and breathtaking West Coast views!
    • Kid-Friendly
    • Accessible
    Sale
  • IDEAL SUMMER TRIP
    Blue skies overlooking a Vancouver Island pier with a blue building in the distance.

    Seaside Sips & Strolls

    $65 USD
    Think waterside strolls, blooming gardens, farm-fresh bites, cozy tasting spots, and storybook towns. This surprise-filled Vancouver Island adventure is packed with charm, quirky detours, and nature escapes you’ll be dreaming about later!
    • Kid-Friendly
    • Accessible
Three women walking through tulip fields
Winding roads through mountains at sunrise

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