Skip the Crowds: 4 Underrated Small Towns to Visit Instead This May

Why Small Town America is the Smartest Trip This Spring

The pull of a big city is strong—the endless restaurants, the famous landmarks, the sheer energy. But as spring arrives, so do the crowds and peak-season prices. This May, we're making the case for a different kind of road trip: one that trades long lines and traffic for historic main streets, genuine local culture, and the simple pleasure of discovering something new.

We've selected four remarkable small towns that shine in the spring. Each offers a compelling alternative to a nearby metropolis you might be considering, giving you all the charm and discovery with none of the hassle. Get ready to reroute your GPS.

Instead of Chicago, Try Galena, Illinois

Galena is a historic city in northwest Illinois, known for its well-preserved 19th-century buildings and its former status as a lead-mining boomtown. While Chicago thaws out, Galena, just under a 3-hour drive west, is already enjoying perfect spring weather.

Forget the Magnificent Mile crowds and instead stroll down Galena's Main Street, which looks like it's been plucked from a history book. Lined with over 100 independently-owned boutiques, antique shops, and cozy cafes, it’s a far cry from the big-city hustle. You can tour the home of Ulysses S. Grant, explore the rolling hills of the Driftless Area, and enjoy a pace of life that actually feels like a vacation.

Instead of Nashville, Try Bardstown, Kentucky

Bardstown is a city in Nelson County, Kentucky, celebrated as the Bourbon Capital of the World and featuring a historic downtown with deep roots in American whiskey production. While Nashville’s Broadway is buzzing 24/7, Bardstown, just a 3-hour drive north, offers a more refined and authentic taste of Southern hospitality.

Here, the star of the show is bourbon. You're at the heart of the Kentucky Bourbon Trail, with legendary distilleries like Heaven Hill and Willett right on your doorstep. The town square is a quintessential slice of Americana, complete with the historic Old Talbott Tavern. It's the perfect place to slow down, savor a dram of world-class whiskey, and soak in genuine small-town charm without the bachelorette party soundtrack.

Instead of Austin, Try Fredericksburg, Texas

Fredericksburg is a city in central Texas, known for its German heritage, numerous wineries, and a historic Main Street lined with unique shops and restaurants. Located about 78 miles west of Austin, it offers a completely different Texas experience.

Swap the tech-hub bustle of Austin for the gemütlichkeit (a German word for a state of warmth and friendliness) of Fredericksburg. Settled by German immigrants in the 1840s, its heritage is on full display along the Hauptstrasse (Main Street), with bakeries serving authentic pastries and halls pouring German-style beers. Beyond the town, you're in the heart of Texas Hill Country wine region, which is gorgeous in May. It's a cultural detour that feels a world away from the capital.

Fredericksburg Historic District Narrated Tour

2 hours · Free Cancellation

★ 4.8 (210)

from $45

Instead of Seattle, Try Port Townsend, Washington

Port Townsend is a Victorian seaport city on the Quimper Peninsula in Washington, offering panoramic views of Puget Sound and the Olympic Mountains. A scenic 2-hour drive and ferry ride from Seattle, it feels like a different world entirely.

While Seattle is a world-class city, Port Townsend is a perfectly preserved slice of Pacific Northwest history. Known for its ornate Victorian architecture, the entire downtown is a National Historic Landmark. You can walk along the waterfront, watch boats sail by with the snow-capped Olympics in the distance, explore the old military batteries at Fort Worden State Park, and browse the many art galleries. It’s a creative, salty-air town that captures the soul of the PNW without the big-city price tag.