A Riverside Ramble
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A Riverside Ramble

A Riverside Ramble

$65.00 USD
Sale Sold out

One trip is required per group.

* "PDF Instant Download" means the trip will be sent by email as a PDF document, and not by mail (the email is sent immediately after completing your purchase)

WHAT TO EXPECT

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.

Trip Highlights

  • A few haunted & strange stories
  • Explore a quirky sculpture park
  • Riverside roaming
  • A brewery in a historic spot
  • The cutest boutiques

AVAILABLE TO DEPART

Available to depart Tuesday - Sunday, throughout the year.

SUGGESTED FOR

  • History or paranormal enthusiasts
  • Groups of friends or families
  • Couple getaways
  • Beginner or advanced cyclists
A Riverside Ramble
A Riverside Ramble
A Riverside Ramble
A Riverside Ramble
A Riverside Ramble

Itinerary

STOP 1

Haunted history or a scenic lookout? This little town really does have it all! Drive time to the second stop is 5 minutes.

STOP 2

Play a little game of eye-spy as you walk between quirky and colorful outdoor sculptures. We've also recommended a handful of boutique shops if you want a souvenir to remember the day. Drive time to the third stop is 10 minutes.

STOP 3

Your third stop offers some incredible riverside gems that will truly take your breath away. Get ready to fill your camera roll! Drive time to the fourth stop is 5 minutes.

STOP 4

Grab a beer at a local spot with the friendliest staff or explore a museum with a unique history!

Region

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Can depart from

Chicago Area, Milwaukee Area

Before you go

What You'll Need to Bring

  • Camera
  • Road Trip Snacks
  • Walking Shoes
  • Water
  • Cash
  • Sunscreen (lots of easy outdoor activities)
  • Bug Spray
  • Reusable Shopping Bags

Additional Details

  • Accessible
  • Kid-Friendly

FREQUENTLY ASKED QUESTIONS

We're here to help!

Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.

From Chicago, IL:

2 hours and 10 minutes / 95 miles

From Rockford, IL:

2 hours and 45 minutes / 140 miles

From Milwaukee, WI*:

4 hours / 230 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

This trip is best done Tuesday - Sunday, any time throughout the year.

You can travel on a Monday; however, a few shops and eateries on stop #4 will be closed.

We recommend departing around 8:30 am if you’re coming from Chicago, and around 7:30 am if you’re coming from Milwaukee. The later you leave, the less time you’ll have to explore all of the stops.

This trip is somewhat pet-friendly! There will be at least one dog-friendly option on every stop. However, note that our shop and eatery suggestions only allow dogs on outdoor patios, so we recommend coordinating with the weather.

We recommend bringing between 2- 5 people on your surprise road trip adventure.

None of the stops on this trip require entrance or parking fees.

*Please note: gas, tolls, and food are additional costs at your own expense.

Yes! All four stops on this trip are close together and connected by a bike path making this trip super bike-friendly! Grab your bike rack & helmet, strap your bikes to your car, and head to the first stop.

We recommend leaving a little bit earlier in the morning if you are planning to bike this trip. The total roundtrip biking distance between all four stops is ~13 miles and is fairly flat, making this a great biking trip for beginner and advanced cyclists.

After booking your trip, we'll send you a confirmation email with a few recommended accommodation options.

Customer Reviews

Based on 2 reviews
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B
Beth Emmerich-Ilecki

This was so much fun. This was a birthday present for my 25 year old. We did it as an overnight. We tried doing everything in each envelope. We ran out of time. Some of the stops were closed for the season. I loved some of the restaurants and shops offered a discount. It would be nice to have a list of things to do at night and dinner restraunts. There is also a cute game shop at stop 2 and a candy shop that was on food network. Life size chocolate work. Just a nice mention for families. If your staying over night purchasing a game is something family friendly

J
Jessica Q
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Best Day Ever!

We loved our first of what I am sure will be many Guess Where Trip! All the trip information was laid out beautifully. One of the locations we had visited previously but on this trip we saw it in a different way and enjoyed it just as much as new locations.