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Windings to Unwind

Connecting Midwesterners to a world full of road-trips, hikes, nature and adventure

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  • Naperville Day Trips (18)
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  • Summer Picnic (18)
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  • Boating (11)

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Recent Posts

  • Road Trip from Chicago during historic Winter Storm
  • Road Trip from Chicago to Pensacola and Florida panhandle
  • Best Chicago Road Trip Memories of 2022
  • Disney World Lightning Lanes + Tips and Park Planning Strategy
  • Chicago to Florida Road Trip – Disney and Key West
  • Road Trip from Chicago to New Orleans
  • Best Winter Road Trips from Chicago
  • Best of Chicago Fall – 2022
  • Road Trip from Chicago to Kentucky Bourbon Trail
  • Hiking at Maple Grove, Downers Grove

Category: Adventure Trips

Best Chicago Road Trip Memories of  2022
Adventure Trips, Spring Break Trips, Summer Road Trips, Winter Road Trips

Best Chicago Road Trip Memories of 2022

As we head into the last hours of 2022, here are the best pictures taken al fresco during my numerous … Continue reading Best Chicago Road Trip Memories of 2022

Road Trip from Chicago to Chattanooga
Adventure Trips, Historical Towns, Long Trips, Spring Break Trips, Summer Road Trips

Road Trip from Chicago to Chattanooga

From chilly to chilling – a memorable spring break road trip from Chicago to Chattanooga. Continue reading Road Trip from Chicago to Chattanooga

Road Trip from Chicago to Red River Gorge, Kentucky
Adventure Trips, Fall Color Destinations, Long Trips, Summer Road Trips

Road Trip from Chicago to Red River Gorge, Kentucky

Summer Adventure road-trip from Chicago to Red River Gorge and Cumberland Falls, Kentucky Continue reading Road Trip from Chicago to Red River Gorge, Kentucky

“No-Regrets – 2022” – Rafting Adventure Road Trip from Chicago to New River Gorge, West Virginia
Adventure Trips, Boys Trip - No-Regrets, Long Trips

“No-Regrets – 2022” – Rafting Adventure Road Trip from Chicago to New River Gorge, West Virginia

No Regrets 2022 – White-water rafting adventure road-trip from Chicago to West Virginia Continue reading “No-Regrets – 2022” – Rafting Adventure Road Trip from Chicago to New River Gorge, West Virginia

9 Summer Road Trip Ideas from Chicago With Detailed Itineraries
Adventure Trips, Long Trips, National Parks, Weekend Getaways

9 Summer Road Trip Ideas from Chicago With Detailed Itineraries

9 curated summer road trip ideas for the best vacation with family or friends. Continue reading 9 Summer Road Trip Ideas from Chicago With Detailed Itineraries

“No-Regrets – 2021” – Rafting Road-Trip from Chicago to Niagara, Wisconsin
Adventure Trips, Boys Trip - No-Regrets, Summer Road Trips, Weekend Getaways

“No-Regrets – 2021” – Rafting Road-Trip from Chicago to Niagara, Wisconsin

No Regrets 2021 – White-water rafting adventure road-trip from Chicago Continue reading “No-Regrets – 2021” – Rafting Road-Trip from Chicago to Niagara, Wisconsin

Road Trip from Chicago to The Great Smoky Mountains
Adventure Trips, Fall Color Destinations, Long Trips, National Parks, Weekend Getaways

Road Trip from Chicago to The Great Smoky Mountains

Road Trip from Chicago to The Smokey Mountains National Park Continue reading Road Trip from Chicago to The Great Smoky Mountains

“No-Regrets 2019” – All Boys Road Trip from Chicago to Rocky Mountains National Park and Colorado Springs, Colorado
Adventure Trips, Boys Trip - No-Regrets, Long Trips, National Parks

“No-Regrets 2019” – All Boys Road Trip from Chicago to Rocky Mountains National Park and Colorado Springs, Colorado

What is No-Regrets A mancation, a tradition, where bunch of close friends hunker down for a weekend of adventure, each … Continue reading “No-Regrets 2019” – All Boys Road Trip from Chicago to Rocky Mountains National Park and Colorado Springs, Colorado

Weekend Road Trip for River Tubing and Sleeping Bear Dunes, Michigan
Adventure Trips, Summer Road Trips, Weekend Getaways

Weekend Road Trip for River Tubing and Sleeping Bear Dunes, Michigan

Why Sleeping Bear Dunes, MI? Tubing on Platte River – One of the best natural lazy river you would find around … Continue reading Weekend Road Trip for River Tubing and Sleeping Bear Dunes, Michigan

“No-Regrets 2018” – Rafting Adventure Road Trip from Chicago to Ohiopyle State Park
Adventure Trips, Boys Trip - No-Regrets, Weekend Getaways

“No-Regrets 2018” – Rafting Adventure Road Trip from Chicago to Ohiopyle State Park

Rafting adventure road trip from Chicago to Ohiopyle State Park Continue reading “No-Regrets 2018” – Rafting Adventure Road Trip from Chicago to Ohiopyle State Park

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