Best Winter Road Trips from Chicago

Why a Winter road trip during holiday season?
Abundance of holidays and warmer temperatures down south lead to a glut of opportunities for Midwesterners to revel in the road trip pleasures and create long-lasting memories in the process.

Criteria for these winter road trips itineraries?
Idea is to focus on warmer places with a lot of sunshine and outdoor activities – both touristy and nature-related.

Here it goes, in the rising order of the distance from Chicago.

1. Branson
Distance: 520 miles.
ETA: 8.5 hours with couple of short breaks.
Why visit?
Holiday Attractions – Polar Express scenic train, Christmas festival at Silver Dollar City – a 1880’s styled theme park which goes all-in during holiday season with 7.5 million lights.

Polar Express Ride. Courtesy :Explore Branson

Polar Express getting kicked off. Courtesy :Explore Branson

An Old Time Christmas. Courtesy: Silver Dollar City

Only a few of 6.5 mil lights! Courtesy: Silver Dollar City

2. Memphis

Distance: 550 miles.
ETA: 9 hours with couple of short breaks.
Why visit?
Plentiful touristy Activities and relatively mild December temperatures. Here’s a short list –
Big River Trail – 70-miles of gorgeous biking trail across the Mississippi levee.

The picturesque Big River Trail, quite a feast 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.
The iconic Beale Street – the home of the Blues and the true birthplace of Rock n Roll. The weather is usually very cooperative as well, amplifying the outdoor experience.
Lastly, you would find ravishing views of The Mighty Mississippi, all around Memphis, that alone is worth the visit!

Big River Trailhead in Dec 2019

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

Big River Trail: You cross over to Arkansas at the half-way mark

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

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

Shelby Farms: A doting mama buffalo. Courtesy: Shelby Farms

You cross over to Arkansas at the half-way mark

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

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

Tip: If you have more days, you can also hop over to Nashville or Chattanooga as part of the trip, they are hardly couple of hours away and have a ton of activities on offer.

3. Smoky Mountains

Distance: 570 miles.
ETA: 9.5 hours with couple of short breaks.
Why visit?
The most visited National Park in the nation offers a ton for the tourists during the holiday season.
Christmas lighting in Gatlinburg and Pigeon Forge, especially SkyLift Park.
More than 350 hiking trails – The day temperatures hit 50s regularly, and the crowds are low, making it perfect to crank through some of the best hikes you would find. I would recommend using AllTrails to plan your hikes.

Check here for a detailed blog listing all activities.

Panoramic views from the SkyLift Park during the day (Courtesy: SkyLift Park)

Twinkling Holidays lights and a giant tree. Courtesy: SkyLift Park

One of many, many scenic overlooks at Smokey

Laurel Falls – one of the highly rated hikes in the region

Not everyday, you get a vacation rental right by the farmstead. Taken during my 2021 summer visit.

A fierce mama bear an the Cades Cove, Smoky trip is incomplete without a bear sighting

4. New Orleans

Distance: 940 miles.
ETA: 15 hours with couple of breaks. You have to start really early though.
Why visit?
Be it the revelries or the iconic food or the vast marshy wetlands or the live music OR the Mighty Mississippi, NOLA is an absolute bliss for all road trip and nature lovers!

Touristy Reasons – Café Du Monde and its highly acclaimed Café Au Lait and Beignet, Audobon: one of a kind insect museum, Louisiana State Museum – The Presbyére, French Quarters, Bourbon Street, Jackson Square, Riverwalk.
Hiking Trails, Louisiana Swamp and Plantation Tours – Cajun Encounters Swamp Tour, Cajun Encounters Plantation Tour, Bayou Sauvage National Wildlife Refuge: a protected marshland noteworthy of swarming wildlife, Barataria Preserve: hike through the celebrated Louisiana marshy wetlands.

Here is the full blog on NOLA.

As seen at Barataria Preserve, courtesy NPS

The iconic Café Du Monde

The rousing views of the Mighty Mississippi, as seen on the way.

A view to inspire Louisiana horror folklore legacy

Plantation Tour, Courtesy: Cajun Encounters

Cypress tress with their intricate knee system

5. Pensacola and Florida Panhandle

Distance: 940 miles.
ETA: 14 hours, a stretch but do-able.
Why visit?

Bayou Marcus Birding Trail, Fort Pickens, Scenic Highway 30A, Tarkiln Bayou Trail, Okaloosa Island Fishing Pier, Pensacola Naval Air Station – home of the Blue Angels, Crabs, Northern Terminus of Florida National Scenic Trail, Fort Morgan.

Water sports should definitely be on the menu as well, but it was too nippy for our December trip.

Check out the full blog here.

Bayou Marcus Trail is entirely on a boardwalk

Sunset #1 – as seen from the Okaloosa Island Pier

Sunset #2 at Fort Pickens Beach

Sunset #3 at Fort Morgan, Alabama

Live pitcher plants at Tarkiln Bayou State Park

Blue Angels at Naval Air Station

A brawny cannon at Fort Morgan

Find Pensacola’s best coffee at Coffee Guy Café

Don’t miss the Northern Terminus for Florida Trail, one of the 11 National Scenic Trails

6. Disney Orlando and Key West

Distance: 1550 miles.
ETA: Have to spread the drive over 2 days.
Why visit?

Disney and Universal theme parks at Orlando, Key West – southernmost city for Continental United States, miles of beaches, wetlands and gators at Everglades Alligator Farm, Kennedy Space Center at Cape Canaveral, Jet Ski/Snorkeling/Pontooning/Parasailing at Fury, congenial weather – what more could you want from the Sunshine State?

Check out the full blog here.

US Route 1, Courtesy Pom’ under Creative Commons