“We travel not to escape life, but for life not to escape us.” – this anonymous quote succinctly captures the spirit of every family planning their next road trip adventure.
Whether you just want a quick 3-hour Weekend Chicago Getaway or have the tenacity for an epic 16-hour road trip to the Rockies as a seasoned road tripper – this mega road trip blog details 14 Road Trips from Chicago with itineraries, pictures and thoroughly researched Things-To-Do.
The ancient ‘New River’ – as seen from the Endless Wall Trail during Chicago to West Virginia road trip
Criteria for these road trips?
Every one of these road trips:
– has plenty of activities for both family and friends, whether it is family-friendly touristy spots, nature outings or adrenaline-pumping activities for thrill seekers.
– has mine (and many other fellow travelers’) first-hand feedback. This is not one of those posts which is *aggregating* stuff already available from Google or your favorite AI search engine.
Without further ado, in order of the *least* travel time from Chicago –
1. Saugatuck and Douglas (Michigan)
Min Days Required: 2 days.
Distance: 200 miles.
ETA: 3 hours.
Why visit?
Saugatuck &Douglas are highly renowned Michigan coastal towns and a great destination for beachgoers, nature lovers and artists.
Find more details here at the official Saugatuck portal.
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Sunset at Oval Beach, Saugatuck
Oval Beach offers great hikes around the rolling dunes in the area
Rolling countryside roads of Saugatuck
Root Beer Barrel Stand at Douglas
Saugatuck Downtown – picture perfect small town charm
Would highly recommend local coffee joint – Uncommon. Courtesy, Uncommon Coffee Roasters
2. Door County (Wisconsin)
Min Days Required: 2 days.
Distance: 280 miles.
ETA: 4 hours.
Why visit?
Door County is not just a Fall Colors novelty, it is truly one of the best weekend getaways for Chicago residents – few hours of drive gets you to a series of tourist-friendly, charming coastal Wisconsin towns bordering Lake Michigan. Door Peninsula is juxtaposed with waters of Green Bay on one side and Lake Michigan on the other, leading to smashing waterfront views.
Taken during Fall Colors Door County Road Trip
Touristy activities – Cherry and/or berry picking, golfing, local wineries and summer festivals.
For Nature Lovers – Biking and hiking at Peninsula State Park (rentals available as well), many other picturesque hiking trails.
Tip: Take a ferry to Washington Island and enjoy almost a day of touristy activities – Cherry Train Tour, Hiking around the island, Lavender farm.
Here is the great official website for list of all Door County activities on offer during summer.
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Biking Ops at Peninsula State Park, Courtesy DoorCounty.com
Local Cherry Train at Washington Island is highly recommended for first time visitors.
Washington Island Stavkirke Church
Schoolhouse Beach, Courtesy DoorCounty.com
Schoolhouse Beach’s famed limestone rocks will massage your feet (and earn a fine if you pocket one)
3. St Louis (Missouri) and Springfield (Illinois)
Min Days Required: 3 days.
Distance: 300 miles.
ETA: 5 hours.
Why visit?
Touristy spots – The iconic Gateway Arch (don’t miss the ride which takes you all the way to the top of the arch), Monstrocity play area with giant slinky tunnels (thrilling for kids and adults alike), Grant’s Farm.
For Nature Lovers – Meramec Caverns, Lone Elk Park (famous for elk, bison and a lot of other wildlife).
For Adventurists – Ziplines at Meramec caverns.
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The Gateway Arch
The Stalactite formations at Meramec Caverns
The Meramec Caverns have rich human history as well
Monstrocity, photo by Laurie Skriva, lskrivan@post-dispatch.com
The center dome at the Capitol of Illinois
4. Adventure Road Trip to Niagara, WI.
Minimum Days Required: 3 days.
Distance: 300 miles.
ETA: 5 hours with many breaks along the way.
Why visit?
Wide assortment of adventure activities for kids and adults, just 5 hours away. Best part is the simplified logistics since lodging, activities and even food is managed by Wildman itself.
White-water Rafting – Wildman Resort is one of the nearest and well-managed white-water rafting spots from Chicago.
Other adventure activities – zip-lining, paintball, kayaking, climbing.
Camping by the Peshtigo River.
Check out the full blog with pictures and itinerary here.
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Heading into the Class-IV rapid at Menominee River
Take a short hike to get a serene view of the Menominee river rapids
Kayaking at the High Falls reservoir
We loved the ziplining as well
Catching a cornhole game while waiting for other activities
The cottages are well-maintained, we stayed at ‘Pine View’
Peshtigo river meandering the resort
Wildman had amateur golfing amenities as well
5. Put-in Bay (Ohio)
Minimum Days Required: 3
Distance: 320 miles.
ETA: 6 hours with couple of breaks.
Why visit?
Quaint Ohio island village on Lake Erie with a ton of family fun/adventure activities. You can also combine it with Cedar Point Amusement Park at Sandusky.
Touristy spots – Benson Ford Ship House, Underground Perry Cave adventure, local wineries, tour train, butterfly house.
Check out the full blog with pictures and itinerary here.
Tip: Also check out the official portal here with infodump on tons of activities.
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Aerial view of the island from the chopper ride (highly recommended)
Feeding frenzy, courtesy African Safari Wildlife Park
Pebble Beaches have crystal clear water
Golf carts are an ideal way to traverse the island
6. Traverse City, Sleeping Bear Dunes, River Tubing (Michigan)
Minimum Days Required: 3
Distance: 360 miles.
ETA: 7 hours with couple of leisurely breaks.
Why visit?
A perfect intermix of water, sand and urban activities.
Touristy spots – Traverse City has something for everyone – vineyards and wineries, dozens of beaches, food and entertainment.
For Nature Lovers – Sleeping Bear Dunes with its emblematic bluffs, dunes and the eponymous Dune Trail to Lake Michigan; canoeing, kayaking and floating at the natural lazy river – Platte River; Biking, paddle-boarding, kayaking, sunset-sails as organized by The River Outfitters and finally, all the camping options.
Tip: Try to merge your road trip with one of the many scenic drives MI has to offer.
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A panoramic sight atop the first hill on the Dune Trail
One of many captivating sights at the Dune Trail
The area has great biking trails, we booked the rentals via The River Outfitters
Floating away at the Platte River, courtesy NPS
MI trip is incomplete without a visit to a vineyard, courtesy Chateau Chantal
Did I mention about Michigan’s acclaimed scenic drives before?
7. Cuyahoga National Park (Ohio)
Minimum Days Required: 3
Distance: 380 miles.
ETA: 7 hours with couple of leisurely breaks.
Why visit?
A lesser known national park but with all the perks.
Touristy spots – Cuyahoga Valley Scenic Railroad.
For Nature Lovers – Brandywine falls, Biking across the historical Ohio/Erie canal Towpath trail and finally, The Ledges Trail, a moderate 1.8 mile hike abundant of vivid rock formations and cliffs, making it truly one of a kind.
Check out the detailed blog with itinerary and pictures here.
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Scenic Railroad (courtesy – Raymond under creative commons)
Cuyahoga River, as scene from the scenic train (courtesy – Alan under CC)
The Ledges Trail – a must visit
One of the many entrancing views at The Ledges
Brandywine Falls
Biking through a partially flooded stretch at Towpath trail was quite an adventure!
8. Red River Gorge (Kentucky)
Minimum Days Required: 4
Distance: 440 miles.
ETA: 8 hours with couple of leisurely breaks.
Why visit?
Rock Climbing/rappelling – Red River Gorge or The Red as it is called, is known for the best climbing crags in the nation, perfect for rock climbing/rappelling.
Underground Kayaking – an exhilarating experience of Kayaking in almost pitch dark in a forgotten underground mine, accompanied by chilling temperatures even when its 90 degrees outside the cave.
Red River – A water fest for the kids: boasting of activities like Cliff jumping, Kayaking, River Tubing.
Scenic Overlooks, trails, scenic drives, streams.
Bonus: Cumberland falls (also known as Niagara of the South) is couple of hours away from Red River Gorge area and the only place in the Western Hemisphere where you can see a moonbow in action.
Check out the full blog with detailed itinerary and pictures here.
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Underground Kayaking, Courtesy Gorge Underground
The Natural Bridge
Suspension Bridge near Red River Jump Rock
Red River Jump Rock
Nada Tunnel, with its one-way traffic, courtesy Cliffview Resort
Miguel Pizza – A ritual for rock climbers/hikers
Cumberland Falls, couple of hours away from Red River Gorge
A swimming hole at Eagle Falls, near Cumberland Falls
9. Mackinac Island
Minimum Days Required: 3
Distance: 440 miles.
ETA: 8 hours with couple of leisurely breaks.
Why visit?
Touristy spots – Mackinac Island is truly one of a kind – with no cars allowed inside, most of the island is preserved as the state park and offers a ton of historical, touristy and nature-friendly activities. No wonder it attracts a bazillion tourists each year.
For Nature Lovers – The 8.2 mile bike trek around the island with serene Lake Michigan views, is as good as it gets. You can also visit Tahquamenon Falls State Park, known for hosting a series of waterfalls plunging into Lake Superior. For those looking a natural swimming holes, you can also take a dip in the Lower Falls at Tahquamenon, a family-friendly swimming site.
Tip: Mackinac Island bifurcates Upper and Lower Peninsula, which gives you a unique opportunity to travel up north to places like Pictured Rock and Soo Locks.. If you want to savor Lower peninsula, you can visit Traverse City and some of other favorites – river tubing at the Platte River and the scenic M31 highway tracing through Elk Rapids, Charlevoix and Petoskey.
Take the M31 instead of I-75, to enjoy a series of highly picturesque coastal towns bordering Lake Michigan
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The Big Mac Bridge, as seen from the beach on the edge of Mackinaw City
The view from our hotel in St. Ignace.
The iconic Arch Rock on the Mackinac Island
The official locomotive at Mackinac
Getting ready to light the canon, at the Fort Mackinac
Fire in the hole!
A monarch taking its flight, at Wings of Mackinac Butterfly Conservatory
Big Mac Bridge from the Mackinac Island StarLine ferry
Tahquamenon Falls – courtesy melodious707 under Creative Commons
The celebrated sandstone cliffs at Pictured Rock, as seen during the evening cruise
Sunset at the middle of nowhere in the Lake Superior
10. New River Gorge at Fayetteville (West Virginia)
Min Days Required: 4
Distance: 570 miles.
ETA: 9 hours.
Why visit?
Adventure activities – white-water rafting, bridge walking, ATV rides, rock climbing, rappelling and a lot more.
A Nature Lover’s paradise – Trails, scenic drives, panoramic vistas, ancient forests, rivers.
Endless Wall Trail is voted #1 trail in the nation in many polls – I have never seen such stunning views accessible via a gentle 2.3 mile out-and-back hike. And all this while, you would hike through the ancient Hemlock forest rich in local flora.
Long Point trail comes a close second, another gentle hike with dazzling views of the symbolic New River Gorge bridge.
Check out the full blog detailing our road trip here.
Tip: The key to visit so many places in a short trip (3-4 days) and not rush through the things, is to simplify the logistics. I stayed and booked most of these adventure activities directly from Ace Adventure Resort whom I found very reliable and resourceful. Would highly recommend Ace Adventure for any of your visits near the area – their Wipeout style water park over an *actual* lake is a kids paradise.
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The New River Gorge, as seen from the Concho overlook
The New River Gorge Bridge (as seen while white-water rafting)
Rafters heading into one of many Class IV/V rapids (as seen while doing Bridge walk)
New River Gorge (as seen from overlook on the Endless Wall trail)
The endless bluffs of the Endless Wall trail
Riding the ATVs through the rugged terrain (and getting stuck)
The ‘Bridge Walk’ on the New River Gorge Bridge
A creepy sign inside the Kayanoor Mine
A waterpark over a natural lake, at the Ace Adventure Resort
11. Smokey Mountains National Park
Minimum Days Required: 4
Distance: 600 miles
ETA: 11 hours with multiple breaks
Why visit?
Plenty of Touristy spots for family – Gatlinburg downtown including Skylift, the Little River Scenic Drive, Pigeon Forge’s amusement parks – huge hit with kids.
For Nature Lovers – Plenty of hiking options, notably – Laurel Falls, Gretto Falls, Clingmans Dom – highest point at Smoky with stunning views, Cades Cove – your best chance at live bear sighting.
For Adventurists – Rafting (we did it with kids as young as 8 at the Lower Pigeon River), Zip-Lining, River Tubing at The River Rat Main Outpost.
Check out the full blog with itinerary and pictures here.
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Rafting at Lower Pigeon River – safe for young kids too
Smokey 101 – The SkyLift Bridge (Don’t miss the night view)
An overlook on the way to Gatlinburg
Laurel Falls
The night view of Gatlinburg atop the SkyLift Park
The view from our cottage – a true country side experience
Bear cub climbing a tree, as seen in Cades Cove
12. Chattanooga and Nashville (Tennessee)
Distance: 630 miles.
ETA: 11 hours with couple of leisurely breaks.
Why visit?
Touristy spots – The Rock City which boasts a vantage point where you could see 7 states, Ruby Falls (underground waterfall), Lookout Mountain (known for the epic Civil War battle), Incline Railway (one of the steepest funicular railway incline in the world), Point Park.
You can also visit Parthenon in Nashville on the way to Chattanooga.
For Nature Lovers – We did the Cherokee Falls trail in Cloudland Canyon State Park. Detailed list of all trails is here.
For Adventurists – Ziplines at Ruby Falls.
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‘Seven States’ point at The Rock City
View from the Lover’s leap overlook at The Rock City
Take the Swing-A-Long bridge, for sure!
Fat Man Squeeze – You will find plenty of constricted entry points at The Rock City
High Falls – 100 ft. man-made waterfalls at The Rock City
Chattanooga Incline Railway – as it looks from the top
Cherokee Falls
A canyon atop the Lookout Mountain, used during the Civil War
An tale of Union Army’s grit, at the Lookout Mountain
One of the many eccentric quotes in our cottage
13. Pensacola (Florida) and Gulf Shores (Alabama)
Distance: 900 miles.
ETA: 14 hours with a few short breaks.
Why visit?
One of the closest ocean fronts from Chicago, Pensacola/Gulf Shores area is renowned for its pristine white sand beaches rich in quartz.
Touristy spots – Fort Pickens, Scenic Highway 30A, Okaloosa Island Fishing Pier, Pensacola Naval Air Station – home of the Blue Angels, Crabs, Fort Morgan.
For Nature Lovers – Bayou Marcus Birding Trail, Northern Terminus of Florida National Scenic Trail, Tarkiln Bayou Trail (known for Pitcher plants).
Water sports should definitely be on the menu as well.
Tip: Nashville area would be a perfect pit stop for this road trip. You can also visit Parthenon on the way.
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Quartz-rich Beaches of Pensacola
Sunsets@Pensacola will satiate desires of most opacarophiles
Fort Pickens has a great beach as well, with a dash of history
Okaloosa Island Fishing Pier is pretty long and provides great 360-degree ocean view
Don’t miss the pitcher plants at Tarkiln Bayou Trail
14. Rocky Mountains National Park
Distance: 1000 miles.
ETA: 16 hours, best to span it across 2 days.
Why visit?
With 400+ miles of mountain environments, 300 miles of pristine hiking trails, sparkling alpine lakes, waterfalls, gushing rivers, meadows and towering mountain peaks, the Rockies tick all the boxes for an epic road trip!
Ethereal view from the Pikes Peak, Colorado
Other Touristy activities – Camping, ATV rides, White-water rafting, driving up or taking a train to Pikes Peak (one of the highest motor-able roads in America), drive to Trail Ridge Road, Bear Lake, Lilly Lake and finally, Garden of the Gods.
Here is the super helpful NPS portal for list of all activities on offer.
Here is the full blog detailing our road trip.
Tip: The weather at the Rockies could be quite shifty, it snowed heavily right before our Memorial Day trip. Please check the official weather updates here.
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While approaching Rockies after 16 hours of driving
Snow clad mountains, as seen from the Trail Ridge Road
Would highly recommend doing the ATV rides, suitable for families as well
Majestic Rocky Mountain Bullhorn Sheep, as seen en route to Chasm Falls Hike
Vistas like above is a routine sight at the Rockies!
Taken en route to Bear Lake
That’s all there is!
If you made it this far, hopefully you found your next road trip adventure from Chicago.
Windings to Unwind 
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