For road trip addicts, Thanksgiving is a great time to rev your engines and go down south where you still have fall-ish weather and plenty of family-friendly activities for creating bucketload of memory dividends (my favorite concept from the must-read Die with Zero book by Bill Perkins).

So, in order of rising travel time, here goes the coveted list:

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

Distance: 270 miles.
ETA: 4+ hours.
Trip Duration: 2-3 days.

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

Why visit?
St Louis is an all-season travel destination for Midwesterners thanks to a plethora of family-friendly activities, amicable weather and short-ish ride from Chicago. The most eminent of these monuments being The Gateway Arch, of course.

IMG_0403
The Gateway Arch

Another must-visit attraction in St Louis is the City Kids Museum, also called Monstrocity; it is brimming with exhibits constructed from many eccentric products. Kids or even adults – would absolutely adore this one, highly recommended!

Monstrocity
Monstrocity, photo by Laurie Skriva, lskrivan@post-dispatch.com

You can also merge St Louis trip with Springfield and see Illinois landmarks like The State Capital, Lincoln Museum and a lot more.

00000IMG_00000_BURST20170331135949_COVER
The centre dome at the Capitol of Illinois

If the underground caves are your thing, Meramec Caverns are a must visit. It offers ziplining opportunities as well.

IMG_0384
The Stalactite formations at Meramec Caverns

2. Louisville and Kentucky Bourbon Trail Road Trip

Distance: 300 miles.
ETA: 5 hours 
Trip Duration: 2-3 days.

The full blog for my  trip is here.

Why visit?
For any bourbon connoisseur pondering over an ever impending bucket list trip to Kentucky Bourbon Trail with their best buddies, two words – Do It! It is totally worth the hype AND a lot more. 

2i5a2122-copy
Using a whiskey thief, at Bardstown, Courtesy Bardstown Bourbon

You could stay at Louisville downtown and go for the tours:

Rickhouse Barrel Thieving Tour at Bardstown Bourbon Co, Bardstown. 
Makers Mark Tour at Makers Mark, Loretto.
Four Roses is widely acclaimed for its alluring, Spanish-style distillery.
Wild Turkey is located atop the rolling hills, giving you an incredible view of the ravishing KY River. 

Here’s what to expect:

You get to stroll around some of the most ravishing landscapes in Kentucky…

PXL_20211113_205225069

And get the best bourbon samplers to test. Below is at Makers Mark:

IMG_6429

You also get to see the iconic Makers Mark sealing process live.

makers_mark_bottle-dipping_1200x630
Courtesy MakersMark

Kentucky Derby Museum is a very noteworthy monument to visit.

2023-tix-popup

Courtesy: Kentucky Derby

So is Louisville Slugger iconic Baseball Museum.

LouisvilleSluggerMuseumFactoryFeaturedExhibitsWalkofFame
Walk of fame at the Slugger Museum, Courtesy Slugger Museum

img_6385
Nothing beats an Old Fashioned at the Bourbon Capital

3. Memphis

Distance: 550 miles.
ETA: ~ 8 hours with couple of short breaks.
Trip Duration: 3-4 days.

Why visit?
Memphis, Home of the blues and Birthplace of Rock ‘n’ Roll, needs no advertising. Music, food, revelry, mild temps, family-friendly touristy activities, it’s got all!

Some recommendations:

Big River Trail – 70-miles of gorgeous biking trail across the Mississippi levee.

Picturesque Big River Trail for the biking enthusiasts

Big River Crossing – a mile-long sky bridge walk on Mississippi cutting through Tennessee and Arkansas with stunning views of the river.
Shelby Farms – Vast public urban park sprawling across 4500 acres, home to bison herd as well. Starry Nights event with dazzling 3.5 million lights is a major attraction during holiday season.
Beale Street – one of the top tourist attractions of Tennessee State – be it food or live music or outdoor activities, this is a huge hit all year.
Graceland – Elvis’s Presley actual home, converted into a museum now. 
Lastly, you would find ravishing views of The Mighty Mississippi, all around Memphis,  that alone is worth the visit!

Mesmerizing Mississippi views on the Big River Trail. Photo courtesy, Big River Crossing

#MildlyInteresting – You hit the AR-TN state border half-way through the Big River Crossing

00000IMG_00000_BURST20191227153217674_COVER


The Mighty Mississippi – As seen from the Riverfront Park in December


Beale Street – Live music, food and festive spirits all year

Shelby Farms: A must-visit dog-friendly public park for all ages. Courtesy: Shelby Farms


Starry Nights at Shelby Farms – Dazzling 3.5 million holiday lights. Courtesy: Shelby Farms

314339196_10158892535149249_2909823835652854633_n

4. Chattanooga (Tennessee) 

Distance: 600 miles.
ETA: 10 hours with couple of short breaks.
Trip Duration: 4 days.

Check out the full blog for more details.

Why visit?
Chattanooga is a terrific catch-all destination for family – be it the Rock City, famous for the rare 7-states lookout point or the iconic Ruby Falls or the gorgeous Lookout Mountain (known for the epic Civil War battle) or the touristy Incline Railway (one of the steepest funicular railway incline in the world, you cannot go wrong with Chattanooga. It is always a big hit with both kids and adults. 

Not to mention, the sweeping views at the Scenic Overlooks –Sunset Rock ViewpointIncline Railway Top Station.

Mocassin-Bend-from-Sunset-Rock-photo-BButters
Scenic Overlook, Courtesy southeasttennessee.com

a0Ff200000LtL62EAFYou gotta stay at the cabins to relish true Southern hospitality. Courtesy: Evolve

PXL_20220329_143333971The swanky pool table at our cottage. Courtesy: Evolve

PXL_20220328_182518195
Ravishing cityscape and the Tennessee River, as seen from the Lookout Mountain

The Rock City is definitely the marquee point of the trip – the mile long hike with gazillion props, expansive views of the lookout mountain, a fun wobbly rope bridge, the constricted pathways; a sublime place for the photo-ops. 

NIK_5431
Scenic point near the waterfall at the Rock City

PXL_20220327_175312874.PORTRAIT (2)
One of many many queer props at the Rock City

PXL_20220327_161734093 (1)
You have to squeeze through many cramped pathways at the Rock City

Ruby Falls – an underground waterfall with stalactites, Stalagmites, Capillary Tubes attract bazillion tourists each year.

NIK_6870 (1)

Chattanooga also houses one of the steepest funicular incline railways in the world, would highly recommend the fun ride.

PXL_20220327_200721971.PORTRAIT

5. Hot Springs (Arkansas)

Distance: 650 miles.
ETA: 10 hours with couple of short breaks.
Trip Duration: 3-4 days.

The full blog for the nature-fueled Hot Springs Road Trip is here. I also find this link helpful to plan your travel. 

img_0695
Enroute to the Hot Springs Mountain Tower

Why visit?

The geothermal natural waters of Hot Springs have been drawing crowds from the time of native Americans. Use this link to find out more about the natural waters and bathhouses as well. 

158B7801
Geothermal Hot Spring, Courtesy nps.gov

Hot Springs National Park itself boasts of numerous biking and hiking trails. Lake Katherine Waterfall is one of my favorite ones.

PXL_20210329_221911067.MP
Lake Katherine Waterfall

The city also boasts of a dedicated baseball trail featuring the activities of baseball legends like Babe Ruth.

_MG_9359
View from our Hot Springs VRBO rental

Other attractions are Talimena Scenic Drive;  Ouachita National Forest – a must-visit for Ziplining, Hiking, Biking and Waterfall enthusiasts and finally, Hot Springs Mountain Tower.

pxl_20210331_204942856
Some great hiking options on Talimena scenic drive.

pxl_20210331_231144080.portrait
Coveted coffee/beer bar on the way to Talimena

Tip: The drive, around 10 hours, is a bit of a stretch if you are not used to long drives but it is actually quite gratifying once you get out of Illinois, especially when you navigate through Mark Twain National Forest (that’s what motivated me for Ozark Camping Trip few months later).

6. New Orleans (Louisiana)

Distance: 950 miles.
ETA: 15 hours with a few breaks.
Trip Duration: 4-5 days.

The full blog for the amazing NOLA trip is here.

IMG_9844
NOLA’s spooky image is quite justified

Why New Orleans or as it is known affectionately, ‘Big Easy’?

Jazz Music – NOLA is arguably, the mecca of Jazz; music embodies heart and soul of the city.

IMG_20191224_221437
Revelry and Architecture – Bourbon Street, French Quarters, Jackson Square, Southern Plantation Tours.

IMG_20191224_214916
A Nature Lover’s Eden – Abundant in swamps, bayous, levees, marshy trails brimming with wildlife sightings including gators and exotic birds.

IMG_20191224_150227

IMG_20191225_135237

Food – Café Au Lait and Beignets offered by iconic Café Du Monde, Po’ boys, jambalaya, gumbo.

That’s it, hope this kindles the desire to take your next memorable Thanksgiving Road Trip.


Like what you see?
View our X or Reddit exploits.


One response to “Best Thanksgiving Road Trips from Chicago”

  1. Great post and wonderful destinations! Thank you for sharing.

Leave a comment

Trending

Create a website or blog at WordPress.com