Start the day with a relaxed departure from Maple Grove and head east to Minnehaha Regional Park for a brisk walk and coffee by the falls before hitting the highway. Continue across the St. Croix River to explore downtown Stillwater-browse antique shops, stroll the scenic riverfront, and grab a late-morning brunch at Café Maude or another riverside spot to fuel the drive into Wisconsin.
After a leisurely brunch in Stillwater, head east into Wisconsin and stop at Interstate State Park on the St. Croix for easy trails and dramatic glacial rock formations along the river-perfect for photos and a short riverside hike. Continue south to Hudson to explore the charming downtown, browse boutique shops on Second Street, and enjoy an afternoon pastry and coffee at The St. Croix Vine & Coffee before settling into a nearby riverside motel or B&B for the evening.
Wind down the day with a riverside dinner at The Boat House Restaurant in Hudson, enjoying sunset views over the St. Croix while sampling regional trout or a hearty burger. After dinner, take a short drive to Tennessee Wolfe Park for a peaceful stroll along lit paths and river overlooks, then settle into a cozy room at the historic Hudson House Bed & Breakfast or a nearby boutique motel to recharge for tomorrow's drive.
Depart your Hudson-area base and head south to explore the quaint river town of Lake Pepin / Pepin Village, where you can stretch your legs along the lakeside promenade and enjoy a morning pastry at Bruski's Bakery before hitting the road. Continue into central Wisconsin with a scenic stop at The National Fresh Water Fishing Hall of Fame in Hayward to browse quirky exhibits and climb the observation tower for wide lake views, then grab a hearty early-lunch sandwich at Stone's Throw Café to fuel the long drive toward Kentucky.
Drive south into central Wisconsin and stop for a relaxed lakeside break at Rib Mountain State Park, where you can take the short Summit Trail for panoramic views and a picnic lunch near the visitor center. Continue toward Madison with an afternoon detour to the quirky House on the Rock complex in Spring Green to wander its eccentric galleries and outdoor gardens before settling into an overnight stay at a comfortable inn in the Madison area.
After a long day on the road, unwind with a relaxed dinner at The Old Feed Mill Restaurant in La Crosse, where you can savor hearty Midwest comfort food and riverside views. Afterwards, take a short post-meal walk along the La Crosse Riverfront to watch the lights dance on the water, then settle into a comfortable night at the nearby Charmant Hotel or another downtown inn to recharge before tomorrow's drive deeper into the Midwest.
Begin your day with breakfast at The Little Hometown Kitchen in nearby Williamstown for scratch-made biscuits and strong coffee before heading to the main attraction. Spend the morning exploring the life-size Ark Encounter-take the guided tour to learn about the massive timber construction, wander the animal exhibits on the Ark's decks, and step into the immersive Creation Museum nearby for complementary displays and gardens that deepen the experience.
After a morning exploring the Ark, take a relaxed lunch and people-watching break at Emzara's Kitchen, sampling homestyle comfort dishes and their famous pies on the terrace. In the early afternoon, stroll the landscaped grounds to visit the interactive Full-size Noah's Ark Exhibit Decks and catch a scheduled ranger talk, then wander over to the nearby Zip Line Adventure for an adrenaline-fueled view of the Ark and Kentucky countryside before grabbing an afternoon coffee at The Ark Store Café to rest up for the evening program.
After a full day at the Ark, enjoy a relaxed evening meal at The Waldo Burr House in nearby Williamstown for Southern-inspired small plates and local brews, followed by a short drive to Williamstown Lake Overlook for twilight views and a gentle lakeside stroll. Finish with a cozy dessert and conversation at Quilter's Cup Café & Bakery, then return to your lodging for an early night or optional stargazing on the grounds to soak in the peaceful Kentucky countryside.
Start your morning with a peaceful walk through The Arboretum, State Botanical Garden of Kentucky, enjoying themed gardens and the duck-filled pond before a coffee and pastry at the on-site Arboretum Café. Continue to Mary Todd Lincoln House for a guided tour that brings local history to life, then stroll down nearby Newtown Pike to browse independent boutiques and an early lunch at Josie's, known for its farm-fresh Southern brunch fare.
Spend a relaxed afternoon exploring the historic horse country charm with a guided tour and tasting at Woodford Reserve Distillery, followed by a scenic drive along Tates Creek Road to visit the picturesque paddocks near Ashford Stud for horse-viewing and photos. Later, wander the lively Distillery District (formerly Gratz Park area) to browse artisanal shops and stop at County Club for craft cocktails and elevated Southern small plates as the sun softens over the bluegrass fields.
As twilight falls, head to the revitalized Manchester Street district for a lively stroll past public art and pop-up shops before settling in for dinner at Doodles Wine & Dine for seasonal Southern plates and a curated wine list. After dinner, catch live music or a late-night craft cocktail at The Burl, then finish the night with a leisurely walk through the illuminated paths of Jacobson Park for peaceful lake views and a gentle end to a day of bluegrass discoveries.
Ease into the day with a hearty Southern breakfast at Main Street Diner in downtown Benton, then wander the nearby historic courthouse square to browse local shops and antique stalls at Marshall County Antique Mall. Mid-morning, take a short drive to Barkley Lake Overlook for waterside strolls and birdwatching, followed by a relaxing paddle or kayak rental from Benton Marina to experience the reservoir and spot scenic coves before a lakeside picnic.
Head south for a scenic afternoon at Reelfoot Lake State Park, where you can take a guided boat tour to spot bald eagles and unique swamp wildlife, or rent a canoe at Reelfoot Lake Outfitters for a quiet paddle among cypress knees. After the lake, swing by Fort Henry Plantation Museum for a short living-history tour and period demonstrations, then sample classic regional barbecue and down-home sides at Rowland's Smokehouse back in Benton before an easy evening stroll along the courthouse square.
As dusk settles, enjoy a farm-to-table dinner at The Green Pig Tavern, savoring seasonal small plates and Kentucky craft beers before heading out for a live-music night at The Barn at Refton Hollow, where local bands play in a cozy, rustic setting. After the show, take a moonlit walk along the levee at Kirksey Lake Park to listen for frogs and night birds, then cap the night with homemade pie and coffee at May's Country Bakery & Café before returning to your Benton lodging.
Leave Benton with a scenic stretch of highway and pause for a riverside coffee and stroll at Mississippi River Overlook Park near Paducah, taking in sweeping water views and historic river markers before continuing west. Mid-morning, detour to Fort Massac State Park for a short interpretive walk among restored fort walls and boardwalks that recount frontier history, then refuel with a hearty lunch at the classic Rafferty's Landing Café in nearby Metropolis before the longer drive toward St. Louis.
After lunch, take a scenic detour to Fort de Chartres State Historic Site for a guided tour of the reconstructed French fort and sweeping views of the Mississippi floodplain, then stroll the nearby prairie trails to stretch your legs. Continue southwest to Cahokia Mounds Historic Site to explore the interpretive center and climb the Monks Mound for a dramatic perspective on pre-Columbian earthworks before settling into a charming St. Louis-area bed and breakfast for the night.
Wind down the day with a riverside dinner at Lindbergh Landing Park & Grill in Cape Girardeau, where alfresco seating and Mississippi views pair well with local catfish or grilled steaks. After dinner, take a twilight walk across the illuminated Bill Emerson Memorial Bridge to admire skyline reflections, then stop for craft beer and live acoustic music at Main Street Pub before checking into a comfortable downtown hotel to rest up for tomorrow's St. Louis explorations.
Start your morning with a brisk walk through Forest Park, pausing to visit the serene grounds around the Saint Louis Art Museum and grab coffee and a pastry at the museum café before hitting the road. Before leaving the city, drive down to the riverside Laclede's Landing for a quick stroll along historic cobblestones and a photo stop at the iconic Gateway Arch Riverfront to capture golden-hour light on the Mississippi.
Drive north from Forest Park to the riverside Citygarden to wander the modern sculpture park and grab a light lunch at Café Osage before a last-city stroll. Then head to the nearby Anheuser-Busch Brewery for a guided tour of the historic brewing complex and sample-room tastings, finishing with a scenic drive out of town along the Great River Road to begin the return leg with river views and a coffee stop at Hermann Hill Winery & Bistro in Hermann if schedule allows.
As the sun lowers, enjoy a convivial dinner at The Hill's iconic Charlie Gitto's for classic Italian-American fare and lively neighborhood atmosphere, then stroll the nearby streets to browse old-world bakeries and gelato stands. Cap the night with panoramic city lights from Belvedere at the Soldiers' Memorial followed by a final drink and live jazz at BB's Jazz, Blues & Soups before beginning the scenic overnight drive north toward Maple Grove.