In 2026, America’s longest highway reaches a major milestone. U.S. Route 20 celebrates its 100th anniversary, marking a century of road trips, exploration, and connection across more than 3,300 miles from Boston, Massachusetts, to Newport, Oregon. Here in Galena Country, Historic Highway 20 winds through some of the most picturesque countryside, and there’s no better way to experience it than with a leisurely road trip from Stockton to Galena to East Dubuque. This stretch of Highway 20 blends rolling hills, historic sites, eclectic shopping, Midwest flavors, and hidden gems you won’t find anywhere else. As communities across the country honor this iconic route, visitors are invited to hit the road and experience the stories, landscapes, and small-town charm that make Highway 20 a true American original. Buckle up and enjoy the journey!
Kick off your Highway 20 adventure in the vibrant village of Stockton, known for its artistic spirit, local flavors, and welcoming small-town charm.
Can't-Miss Places in Stockton
Stockton Pit Stop – Fuel up! Literally and figuratively, with snacks, coffee, or a quick bite before you hit the road.
Mud Run Beer Co. – A Driftless craft brewery serving small-batch beers in a cozy, friendly environment. Great food options, too!
Stockton Murals – Explore colorful public art celebrating local history and community pride. They make perfect photo ops!
Sweet Alice’s – A nostalgic candy and tea shop offering treats for every age (don’t miss their fudge).
Beautifully Berkeley Bouquets & Home – A beautifully curated boutique offering home goods, gifts, and handmade treasures.
Savvy Scavengers – A chic, trend-setting boutique offering stylish apparel, unique accessories, and curated fashion finds you won’t see anywhere else.
With your morning shopping and snacking complete, jump back on HWY 20 and take in the rolling farmland that leads toward Woodbine.
Highlights in Woodbine
Woodbine Bend Golf Course – This scenic, link-style 18-hole course offers sweeping countryside views and a relaxed yet engaging play experience.
Nature's Treasures – A local favorite for plants, crystals, gifts, books, and earth-inspired items.
After a quick stretch or a round of golf, continue toward Elizabeth—and make sure your camera is ready.
Elizabeth is a must-stop destination along Historic Highway 20. You'll find hearty lunches, antique browsing, and unique boutiques throughout this charming village.
Essential Experiences in Elizabeth
Highway 20 Brewing Co. – Start off your Elizabeth visit with a craft beer brewed on-site, featuring rotating taps, small-batch flavors, and a laid-back atmosphere perfect for relaxing along your Highway 20 journey.
Lola’s Deli – Known for fresh sandwiches, soups, and friendly service—perfect for a road-trip lunch.
The Clothes Bin & Gift Shop – A stylish local boutique featuring apparel, accessories, and gifts.
Common Cents Resale – A treasure trove for bargain hunters and vintage lovers.
Terrapin Station Café – Grab a cup of locally roasted coffee or a sweet treat.
Elizabeth’s Grand Antique Co. – One of the region’s largest antique malls with more than 200 vendors. There's even a coffee shop and wine bar inside!
Just west of Elizabeth, pull over at the iconic Longhollow Scenic Overlook for panoramic views of the Driftless Region’s rolling hills, a highlight of any HWY 20 journey.
Continuing west brings you into Galena, one of the Midwest’s most beloved small towns, rich in 19th-century architecture, outdoor experiences, and iconic attractions.
Food, Lodging & Adventure in Galena
Highland’s Restaurant – An inviting, upscale-casual dining experience at The General Golf Course, offering thoughtfully crafted favorites and warm hospitality in a refined yet relaxed setting, perfect for lunch or dinner.
The General Golf Course at Eagle Ridge Resort & Spa – Set in the heart of The Galena Territory, this award-winning course is both challenging and breathtaking.
Dry Creek Beekeeping – Explore the fascinating world of pollinators through hands-on learning, taste locally crafted honey, and shop artisanal beeswax products while discovering the important role bees play in the Driftless Region.
Hoof It Goat Trekking – Hike alongside friendly goats for a uniquely Galena adventure.
Galena Goat Yoga – Stretch, laugh, and unwind with playful goat companions.
Irish Cottage Inn & Suites & Frank O’Dowd’s Irish Pub – An immersive Irish experience with live entertainment, hearty fare, and warm hospitality.
Ulysses S. Grant Home State Historic Site – A beautifully preserved home gifted to the Civil War general upon his return from war.
Belvedere Mansion & Gardens – A Victorian masterpiece offering guided tours full of rich history and ornate décor.
Galena’s Historic Main Street – More than 125 shops, wineries, galleries, bars, and eateries line this iconic, walkable street.
Hotel Galena, Farmer’s Guest House, Stoney Creek Inn & Wyndham Garden Galena – Whether boutique charm or resort-style relaxation is your style, Galena offers top-notch accommodations.
After exploring, continue west as HWY 20 twists toward the Mississippi River valley.
Worth-the-Drive Spots in Menominee
Hilltop at Menominee – A welcoming restaurant and bar offering hearty meals and sweeping countryside views.
Berning Acres Farms – A family-owned dairy farm offering interactive tours, seasonal events, and an inside look at farm life.
What to Explore in East Dubuque
Millennium Bar & Marina – Known for cold drinks, live music, and unbeatable river views.
Midtown Marina – A favorite for boating, cocktails, and casual eats right on the water.
Timmerman’s Supper Club – An elegant Midwest classic perched high above the river, famous for prime rib, seafood, and sunset views.
Cruisin’ Thursdays – A seasonal downtown event featuring classic cars, live music, food, and community fun.
Start Planning Your Historic Highway 20 Road Trip
Historic Hwy 20 offers a blend of small-town shopping, iconic Midwest eateries, outdoor recreation, and unforgettable scenic views. Whether you're road-tripping for a day or exploring the route over a weekend, this itinerary highlights the very best of the Stockton through East Dubuque journey through Jo Daviess County.
As Historic U.S. Highway 20 celebrates 100 years of connecting communities and inspiring adventure, there’s never been a better time to hit the road and experience this unforgettable stretch through Galena Country. From scenic overlooks and charming downtowns to local flavors and hidden gems, every mile tells a story. Start mapping your route, book your stay, and make your own memories along America’s longest highway. For even more trip inspiration, download the Galena Country app and request a free Visitor Guide to keep your road trip rolling.