9 Summer Road Trip Ideas from Chicago With Detailed Itineraries

Why a road trip during Summers?
For Midwesterners, summer is a precious commodity. After all, you only get few months of relief against the several layers of clothing you need to adorn all along the year to succeed in your warfare with the callous Chicago weather.

And the additional summer daylight provides a vital impetus to both travel as well as sightseeing.

Criteria for these road trips?

The place should within a day’s drive (10 hours threshold) and have a plethora of activities in three main areas – adventure, nature and touristy spots.

1. New River Gorge at Fayetteville (West Virginia)

Distance: 570 miles.
ETA: 9 hours.
Why visit?
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. As a bonus, you 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 details here.

Tip: The key to visit so many places in a short trip (3-4 days) and not spend enormous time in planning, 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 similar strategy for others to enjoy more and plan less.


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

2. Smokey Mountains National Park

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 here.


Rafting at Lower Pigeon River

Smokey 101 – The SkyLift Bridge

An overlook on the way to Gatlinburg

Laurel Falls

The night view of Gatlinburg atop the SkyLift Park

PXL_20210619_002837662 (1)The view from our cottage – a true country side experience 

Bear cub climbing a tree, as seen in Cades Cove

3. Mackinac Island

Distance: 440 miles.
ETA: 8 hours with couple of leisurely breaks.
Why visit?
Touristy spots – Mackinac Island is truly one of a kind – 8 miles long with no cars allowed inside, most of the island preserved as the state park and a ton of historical and architectural magnificence on offer. No wonder it attracts a bazillion tourists each year.
For Nature Lovers – The 8.2 mile bike trek around the island, with Lake Michigan giving you company all along, 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. 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 and if you want to savor Lower peninsula, you can visit Traverse City and some of other my favorites – river tubing at the Platte River and the scenic M31 highway tracing through Elk Rapids, Charlevoix and Petoskey.

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Take the M31 instead of I-75


The Big Mac Bridge, as seen from the beach on the edge of Mackinaw City

IMG_20160724_081426The view from our hotel in St Ignace.

IMG_8045The iconic Arch Rock on the Mackinac Island

IMG_4122The official locomotive at Mackinac 

Getting ready to light the canon, at the Fort Mackinac

And there it goes..

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

4. Traverse City, Sleeping Bear Dunes, River Tubing (Michigan)

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

Kids being kids, at the Dunes Trail

Biking trip, booked via The River Outfitters

Floating away, at the Platte River

MI trip is incomplete without a visit to a vineyard, courtesy Chateau Chantal

Did I mention about Michigan’s scenic drives before?

5. Red River Gorge (Kentucky)

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 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.

See the full blog here.


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

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Cumberland Falls, couple of hours away from Red River Gorge

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A swimming hole at Eagle Falls, near Cumberland Falls

6. Cuyahoga National Park (Ohio)

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 details here.


Scenic Railroad (courtesy – Raymond under creative commons)

Cuyahoga River, as scene from the scenic train (courtesy – Alan under CC)

Kids enjoying the scenic drive

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

7. Adventure Road Trip to Niagara, WI.

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 RaftingWildman 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 details here.


Heading into the Class-IV rapid at Menominee River

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An exclusive view of the Menominee river rapids

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Cliff Jumping during Kayaking trip

Kayaking at the High Falls reservoir 

Ziplining at the resort

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Catching a cornhole game in between the activities

Our cottage rental

Peshtigo river meandering the resort

Amateur golfing amenities

8. St Louis (Missouri) and Springfield (Illinois)

Distance: 300 miles.
ETA: 6 hours with couple of leisurely breaks.
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.


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

The full blog for the vivid St Louis trip is here.

9. 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.


‘Seven States’ point at The Rock City

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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

That’s it!

Hopefully, this blog helps you get behind the wheels and take a memorable road trip with your loved ones.

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2 thoughts on “9 Summer Road Trip Ideas from Chicago With Detailed Itineraries

  1. Awesome post — I’ve been over that bridge and it is wild!
    If you go that way again, check out Middleboro, Ky— it’s just a mountain town, but it was build in an asteroid crater about ten miles wide.

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