The Great Autumn, Urban Roadtrip Escape!

Five urban destinations perfect for a getaway road trip this fall

By Laura Hennigan / Story Design by Tori Smith

As the days begin to shorten and the air starts to feel a little more crisp, you know that autumn is on its way.

And there’s no better way to experience the seasons than from a cozy Main St. coffee shop, winding your way through a tree-lined campus, or browsing a local indie bookstore.

We’ve rounded up the most charming college towns perfect for a weekend getaway this fall, and you can get to each one in about five hours or less.

Lexington, Kentucky

Tucked into the rolling hills of the Bluegrass region, you’ll find Lexington, known for horses, bourbon and the University of Kentucky. Many people start their visit at the famous Kentucky Horse Park, a working horse farm and equestrian competition venue where you can get up close and personal with many different breeds. Or amble around the park-like Keeneland Race Course, where the grounds are open to the public and you can catch a glimpse of horses on the track for their morning workouts.

Lexington itself is full of numerous historic sites and museums, including the Mary Todd Lincoln House and the Henry Clay Estate. As you wander the city, you’ll also discover beautiful, imaginative, and thought-provoking art just about everywhere you look, thanks to over 50 street murals. Whether or not to imbibe at one of the many distilleries is up to you, but either way plan to grab a tasty Kentucky Hot Brown sandwich, originally made famous in nearby Louisville.

Knoxville, Tennessee

There’s something for everyone in eclectic Knoxville, which manages to retain a small-town feel even with the presence of the University of Tennessee campus (be sure to pack something orange to wear). There’s a laid-back vibe wherever you go, from the historical Civil War walking and driving tours to the award-winning, vibrant restaurant scene. Check the calendar to see what’s happening in Market Square, which hosts live music, festivals and fairs throughout the fall.

Be sure to explore one of the many outdoor options, including the Knoxville Botanical Garden & Arboretum and the World’s Fair Park, where you can get a 360 degree view of the city from the Sunsphere observation deck. Or head a little further afield to check out the Knoxville Urban Wilderness, a massive outdoor space offering 50 miles of trails where you can bike, hike, climb and paddle. After a full day of adventuring, spend some time in Old City, a charming neighborhood full of shops, cafes, galleries, and breweries that offer something for everyone.

Bloomington, Indiana

As the home of Indiana University, Bloomington embodies classic small-town Americana. The highly walkable downtown area is full of unique restaurants, shops, bars, and venues, particularly on Kirkwood Avenue, the city’s most iconic street. Spend a day wandering between small art galleries and boutiques, then cap off your evening at the Buskirk-Chumley Theater, a Spanish mission revival silent movie house that hosts music, dance, film, and community events.

Venture out a little ways and you’ll find many outdoor adventure options, like kayaking and fishing at Monroe Lake, or hiking some trails in Hoosier National Forest. There are unlimited options for every meal, and the restaurants here are so diverse that the city’s dining slogan is “Bloomington: A World of Food.” Be sure to check out Samira’s, a unique restaurant that combines Mediterranean, Afghan, and Middle Eastern ingredients in its dishes. End the day by heading over to Switchyard Brewing Co. or Metal Works Brewing Company to enjoy a locally-crafted brew, or visit the toprated Oliver Winery & Vineyards, Indiana’s oldest winery.

Ann Arbor, Michigan

We know, we know, but hear us out: take away the whole football thing, and Ann Arbor is actually a lovely place to spend a weekend. It’s developed into quite the foodie paradise, with dozens of locally-owned restaurants and breweries that invite both visitors and locals to enjoy a wide variety of diverse offerings. The city is also known for its globally-inspired cultural offerings, and is home to renowned galleries and museums, as well as theatrical and musical performances from local, regional, and international artists.

Spend a quiet afternoon perusing Literati Bookstore, which was named bookstore of the year by Publishers Weekly in 2019, then head over to the Main Street area for plenty of boutique shopping. See the “arbor” parts of this leafy locale from the water after renting canoes or kayaks from the Argo Park Livery. Wrap up your time with a Reuben at Zingerman’s deli, followed by drinks and live music at either The Ark or the Blue Llama Jazz Club.

Charleston, West Virginia

While anywhere in West Virginia is a dream in the fall, the state capital of Charleston is a safe bet to maximize your Mountain State experience. Boasting a population of nearly 50,000, the state’s most popular city offers its own urban charm, situated at the confluence of the Elk and Kanawha Rivers. There are plenty of museums and markets in addition to the bustling Capitol Street, lined with historical buildings and unique businesses.

Located near the center of the state, Charleston is within a reasonable distance of some of West Virginia’s–and consequently, the country’s–most beautiful autumn landscapes. The New River Gorge, which is nothing short of breathtaking in the fall, and features a National Park, one of the country’s most iconic bridges (The New River Gorge Bridge) and more, is just over an hour away. Holly River State Park, the Monongahela State Forest, Blackwater Falls State Park and more are within a drivable distance, and in the fall in West Virginia, the drive is part of the experience.