Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell

Post originally Published December 13, 2023 || Last Updated December 14, 2023

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Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Rolling Along the Fox River Valley

Just an hour west of the Windy City lies the bucolic landscapes and quaint river towns of the Fox River Valley. This area offers a perfect easy day trip escape from the hustle and bustle of Chicago into a world of rolling hills, cycling trails, and river cruises.

Start your Fox River adventure in St. Charles, Illinois, located on the banks of the river. Pop into the historical Boy Scout cabin, which dates back over 100 years and now serves as a museum. Then rent a bike and hit the nearly 20 miles of scenic trails that wind through St. Charles. Pedal over the river and through serene natural areas filled with wildlife.

Further upstream, don't miss a stop in Geneva, which boasts over 25 blocks of historic buildings and homes dating back to the 1830s. Take an architecture walking tour to take in the Gothic Revival and Queen Anne style mansions. Then relax at one of the town's cozy cafes after working up an appetite while walking.

No trip to the Fox River Valley is complete without a riverboat cruise. Glide along the water for incredible views of the lush bluffs and valley. Many cruises even feature live music, dining, and specialty drinks for a truly memorable experience. Choose from public cruises or private charters depending on your preference.

Round out your Fox River adventure with a drive through the surrounding countryside. While the river towns are undoubtedly charming, some of the best scenery is found on the rural roads. Stop at roadside farm stands and markets for fresh produce. Discover historic barns and covered bridges straight out of a painting.

What else is in this post?

  1. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Rolling Along the Fox River Valley
  2. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Paddling Through the Dunes of Indiana
  3. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Frank Lloyd Wright's Architectural Gems
  4. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Rural R&R in Galena
  5. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Trails and Waterfalls of Starved Rock
  6. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Quaint Charms of Lake Geneva
  7. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Caving Adventure in Maquoketa
  8. Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Rustic Getaway to Kohler-Andrae State Park

Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Paddling Through the Dunes of Indiana

Looking to swap skyscrapers for sand dunes? Just 90 minutes from Chicago, Indiana's shoreline along Lake Michigan transports you to a world of rugged natural beauty and limitless aquatic adventure. Grab your kayak, canoe or stand up paddleboard (SUP) and head to the Hoosier State for an unforgettable paddling experience.

The crown jewel of Indiana's "Gold Coast" is the Indiana Dunes National Park, spanning 15,000 acres with over 70 miles of shoreline. Expert paddlers can traverse the length of the park, exploring coves, inlets and the Little Calumet River. Novices are best suited sticking to the sheltered and shallow waters of Lake Michigan near West Beach or the East Arm. Regardless of your skill level, be sure to paddle out to see the park's famous singing sands. A bizarre natural phenomenon causes the sand to squeak or sing when walking across it, resulting in an almost musical quality.

Just 10 minutes from the Indiana Dunes National Park, try a relaxing paddle along Trail Creek in Michigan City. This sheltered estuary provides an intimate experience, with opportunities to spot turtles, herons, and other wildlife. Rent a kayak or canoe right on-site from Trail Creek Marina and spend a leisurely few hours on the water. Stop at the beach for a picnic lunch before heading back.

If you're looking for a scenic river paddle, head just outside Michigan City to Kankakee River State Park. Sign up for a naturalist-guided kayak tour, offered on Saturdays and Sundays during summer. Learn about the unique ecology of the region as you drift along this winding waterway. Pack a lunch to enjoy at one of the peaceful sandbars mid-journey. Self-guided rentals are also available if you'd rather chart your own course.
No Indiana paddling adventure is complete without experiencing the dune-flanked Galena River. Rent kayaks or canoes from Joe's Rent-All and embark on a 5-mile downstream journey from La Porte to potato creek. Gaze up in awe at the sandy slopes rising high above you. Search for river otters playing along the banks. Allow 4-5 hours for this paddling experience – you'll be stunned by how quickly the time flies.

Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Frank Lloyd Wright's Architectural Gems

No trip to Chicago’s environs is complete without paying homage to one of America’s most iconic architects, Frank Lloyd Wright. Though Wright’s magnum opus of Fallingwater may be far from the Windy City in Pennsylvania, three of his prairie-style masterpieces can be found right in Chicago’s backyard.

First up is the Frederick C. Robie House in Chicago’s Hyde Park neighborhood. Built between 1909 and 1910, this building exemplifies Wright’s pioneering explorations in open plan living. The interior spaces effortlessly flow together under sweeping horizontals, while ribbons of art glass windows usher in natural light. Despite some additions by later owners, the Robie House retains one of the most intact Wright-designed interiors in the country. Tour the home to admire the unbelievable attention to detail, from custom-designed furniture to signature architectural motifs. Don’t leave without snapping a photo of the front exterior staircase – an icon of modernist architecture.

Travel next to Oak Park, Wright’s hometown, now home to the largest single collection of Frank Lloyd Wright-designed buildings. Here you’ll find two gems: Wright’s own Home and Studio as well as the Unity Temple. Wright lived and worked out of his Home and Studio from 1889 to 1909, and this building marked the birth of his signature “prairie” style. Unity Temple, completed in 1908, represents one of Wright’s first masterpieces. This Unitarian Universalist church fully embraces his philosophy of organic architecture with exposed interior woodwork and unconventional shapes. Both buildings offer tours – a must for any architecture buff.
Finally, make your way 45 minutes north of Chicago to Wright’s Temple near Fontana-on-Geneva Lake, Wisconsin. Blending in seamlessly with its wooded surroundings, this former Unitarian Universalist church perfectly epitomizes Wright’s organic vision. Completed in 1955, the triangular structure lacks right angles. Concrete “tree trunks” support the roof, while signature textile blocks filter light. Even if you can’t get tickets to a Sunday service, you can explore the grounds and interior during open public tours from May through October.

Visiting Wright’s work firsthand provides an unparalleled opportunity to immerse yourself in the mind of an architectural genius. Tour guides will share insightful stories and bring these spaces to life. Seeing Wright’s prairie-style up close sheds light on its main principles, like openness, horizontality, and simplicity. You’ll gain a new appreciation for how his spaces foster community and connection. Beyond surface appearances, Wright’s buildings have an incredible intentionality behind every detail.

Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Rural R&R in Galena

Nestled amidst rolling hills and dense forests along the Galena River sits the quaint village of Galena, Illinois. Just 165 miles northwest of Chicago, this charming small town transports visitors back in time with its wonderfully preserved 19th century buildings and stone architecture. Galena provides the perfect antidote to big city stresses through its slow pace, fresh air, and abundance of outdoor recreation.

Upon arriving in Galena’s nearly perfectly preserved downtown, you’ll feel instantly transported back to the mid-1800s when it thrived as lead mining and steamboat hub. The 9 city blocks of Main Street feature over 85% original buildings, yielding the finest intact example of a mid-19th century commercial district in the country. Wander along Main Street and explore highlights like the 1826 Dowling House, an Irish stone cottage, and the 1845 Old Market House, converted from Galena's original city hall and marketplace.

Beyond its architectural wonders, Galena offers plenty for the outdoor enthusiast. Lace up your hiking boots and head to the Galena River Trail to traverse nearly 10 miles along the waterway. Gaze up at sculpted limestone cliffs and keep eyes peeled for wildlife like river otters and herons. Or choose from over 30 miles of trails within Jo Daviess Conservation Area for scenic walks through rolling terrain where the Mississippi Palisades begin.

In autumn, pick apples at one of Jo Daviess County's many orchards, like Apple River Fort and Elizabeth Orchards. Or embark on a relaxing paddle down the Galena River - you’ll feel a million miles from the big city surrounded by colorful fall foliage. Come winter, discover why Galena is dubbed the "Midwest's Most Idyllic Winter Town." Snuggle into your coziest sweater for a horse-drawn sleigh ride, or rent snowshoes to trek through the snowy forests. Sip hot cocoa after an afternoon spent tubing, cross country skiing, or taking a winter cave tour.
At day's end, cozy up by the fireplace in one of Galena's charming inns and B&Bs housed in historic buildings. Savor delicious farm-to-table cuisine showcasing local ingredients at restaurants like One Eleven Main. Or opt for casual comfort fare and local brews at a place like Fried Green Tomatoes. You'll sleep soundly amidst the peaceful silence, waking ready for more small townDiscovery.

Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Trails and Waterfalls of Starved Rock

Just 100 miles southwest of Chicago lies Starved Rock State Park, an oasis of wilderness that transports visitors to a world of roaring waterfalls, soaring canyons, and glacier-carved bluffs. This geologic gem situated along the Illinois River glimmers like a hidden jewel, inviting weekend adventurers to uncover its incredible natural beauty mile after mile. With 13 miles of hiking trails to satisfy any ability level, Starved Rock offers the ideal easy escape into nature without venturing far from the big city hustle.

Lace up your most comfortable shoes to embark on Starved Rock’s trails, which deliver payoffs of magnificent waterfalls around nearly every bend. The park’s 18 seasonal cascades tumble over sandstone cliffs, spill down mossy ravines choked with ferns, and splash across boulder-strewn streams ideal for wading. Don’t miss standouts like the 60-foot-tall St. Louis Canyon waterfall – the longest continual drop in the state – where adventure seekers can even scope out the torrent from behind its thundering veil. Or admire the wide and gentle LaSalle Canyon falls, flanked on either side by curving tan walls that resemble a giant’s footsteps carved out of stone.

While the waterfalls act as the headlining attraction, the scenic hiking trails themselves charm just as much with their diversity. Meandering dirt paths lined with walnut and oak trees draw you deeper into secluded box canyons, then deliver stunning ridgetop panoramas of the park snuggled between verdant bluffs and the glinting river below. The iconic Illinois Canyon trail showcases it all via a figure-eight shaped route – cascades, canyon views, and 100-foot rock walls ideal for amateur climbers. Families relish easygoing trails like the River Walk for level terrain and river vistas, while avid hikers opt for the rocky challenge of the Wildcat Canyon loop.

Although each person’s experience on the trails differs, most agree Starved Rock offers a restorative escape from concrete jungles. Bloggers describe the childlike wonder rediscovered when happening upon surprises like moss-cloaked waterfalls and rocky outcrops perfect for perching. Avid hikers praise the diversity satisfying short jaunts and lengthy treks alike. Families revel in navigating the trails together – wading in cold cascade pools, tracing names into canyon walls, and sharing trail mix under a sunny ridge. Despite sore feet and tired legs, many emerge rejuvenated by nature’s splendor.

Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Quaint Charms of Lake Geneva

Nestled alongside sparkling Lake Geneva, the town of the same namesake has beckoned weekend escapists from Chicago for over a century. Just an hour and a half northwest from the Windy City, Lake Geneva transports visitors to a quainter time with its historic architecture, laidback vibe, and timeless lakefront pursuits.

Wander the compact downtown district to admire stately 19th century buildings now housing eclectic shops, cozy cafes, and ice cream parlors serving up nostalgia by the scoop. Pop by the legendary Baker House, built in 1885 as one of the area's first hotels. Despite Lake Geneva’s small size, over 50 buildings are listed on the National Register of Historic Places for architecture buffs to uncover.

At the heart of downtown sits scenic Flat Iron Park, named for its triangle-shaped plot of land. Unwind on a bench under the shade trees and watch boats lazily drift by just steps away. Or spread out a picnic blanket and savor local cheese, fruit, and other edible souvenirs from downtown shops. Kids especially love climbing on the park's landmark WWI Doughboy statue, a Lake Geneva tradition.

Of course, no trip to Lake Geneva is complete without some quality time on the water that gives this town its name. Join locals putting along the shoreline by renting your own kayak, paddleboard or pontoon from outfitters like Gage Marine. Paddle out to Black Point Estate and Gardens for a self-guided waterfront tour – the only way to experience these immaculately manicured grounds is by boat. Avid anglers can cast a line for bass, walleye, and panfish easily from shore at one of the many lakefront parks.

Come late afternoon, claim your spot on the beach to watch a glowing orange sunset melt into the horizon. Riviera Beach hearkens back to the classic days of sandy swim spots, concession stands, and beachfront estates. Or escape to quieter and more secluded Williams Bay Beach bordering a bird sanctuary. Wherever you choose to post up, Lake Geneva sunsets rarely disappoint with their stunning bands of color.

As dusk falls, experience Lake Geneva’s old-fashioned charm on a relaxing horse-drawn wagon ride. Teams of Belgians and Percherons clip-clop through town, providing unique views of tree-lined neighborhoods and exclusive lakefront estates. Listen to fascinating historical commentary from knowledgeable guides detailing the lavish residences and storied past. Nighttime trips evoke nostalgia, with streetlights and buildings glowing against the inky sky.

Before calling it a night, cozy into one of downtown’s atmospheric restaurants housed in historic buildings. Savor Italian classics on the vine-covered patio at Sprecher’s, the oldest restaurant in Lake Geneva. Slip into a red leather banquette booth at The Next Door Pub, pouring local brews since Prohibition. Or toast to new adventures and new friends over family-style Greek and American fare at Savor's Wine Bar.

Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Caving Adventure in Maquoketa

Tucked away just outside the Iowa town of Maquoketa lies a subterranean world of twisting passages, lofty chambers, and icy cold underground rivers - a realm best explored by those craving caving adventure.

The Driftless Area of Iowa, carved by the Mississippi River's ancient currents, hides over 150 known caves - and Maquoketa Caves State Park protects the most accessible and stunning among them. Come prepared with sturdy shoes, headlamps, and warm layers to uncover the natural splendor lying beneath the rolling prairie grasses.

Descend into Dancehall Cave, where ceiling heights reach up to 50 feet, and imagine pioneers waltzing under the flickering light of lanterns at 19th century balls. Wander through more than a half-mile of interconnected rooms, tracing your hand along pockmarked limestone walls and ducking under low-hanging rock ceilings smoothed by eons of water.

Nearby Bear Cave envelopes explorers snaking through its tight passageways with total darkness, testing your mettle as you crawl on hands and knees through the inky black void. Emerge on the other side thrumming with adrenaline, your headlamp illuminating glittering rock formations as reward.

For a shorter but exhilarating adventure, shimmy through the Fat Man's Misery crack - you'll suck in your gut squeezing through the 10-inch crevice into Eclipse Cave beyond. Gawk at canyon-like walls towering above, then scout for bats fluttering in the shadows.

The park's jewel is 50-foot-tall Balanced Rock, precariously perched atop a limestone pedestal. Scramble over breakdown boulders, soggy with centuries of calcite-threaded water, keeping eyes peeled for this gravity-defying formation. Load up your camera - there's no bad angle when photographing Balanced Rock.

Caving newbies0069 often remark on the mental focus required inside Maquoketa's caverns - with no phone signal or daylight as distraction, senses heighten to narrowly avoid bumps and bruises as you forge ahead. Despite challenges like claustrophobia-inducing spots, they emerge feeling accomplished after pushing their personal limits.

Avid spelunkers highlight the diversity satisfying both novice and expert. Scrambles over slippery breakdown and chimney climbs up fissures appeal to hardcore cavers, while walk-in caves accommodate families. Maquoketa also offers multi-hour routes connecting various caves for an all-day subterranean trek.

Windy City Weekenders: 7 Epic Day Trips to Escape Chicago for a Spell - Rustic Getaway to Kohler-Andrae State Park

Nestled along the Lake Michigan shoreline, Kohler-Andrae State Park transports weary souls from Milwaukee and Chicago to a world of sandy beaches, dense forests, and tranquil sunsets. Just an hour north of Milwaukee, Kohler-Andrae delivers an easy escape to simplicity for those craving some rustic R&R.

Venture down two miles of pristine beach, where Lake Michigan’s waves wash the shoreline clean daily, leaving behind smooth pebbles that click-clack underfoot. Search for Petoskey stones glimmering in the sand, their hexagonal fossils exposing Michigan’s ancient past. Out on the sage-hued water, watch windsurfers dance atop the waves as gulls circle hungrily overhead.

Inland from the beach stretches a densely wooded forest threaded with over seven miles of trails ideal for renewing both body and spirit. Breath deep to fill your lungs with crisp air to cleanse away city smoke. Listen to songbirds serenade and chipmunks scurry amidst the crunch of autumn leaves. Pause beneath a towering hemlock, its feathery branches filtering sunlight down in shifting shadows, as a meditative reset for your senses.
After working up an appetite, gather ‘round glowing fire pits to roast hot dogs and s’mores until ooey-gooey. New friends swap stories and laughs that lift spirits as effortlessly as smoke dissipates into the night sky. When heavy eyelids hint at the late hour, zip into tents while owl hoots and cricket chirps sing you to sleep.

Rise with the morning mist off Lake Michigan, refreshed and ready to greet the new day. Perch on driftwood under pastel skies for front row seats to the sunrise, as birds awaken and waves crescendo in a natural symphony. Then wander over to the Nature Center, where attentive rangers help identify animal tracks, edible plants, and other forest mysteries that reveal themselves to patient observers.
Don’t depart without a scenic stroll along Black River as it winds through the park, lined with marshland, evergreens, and wildflowers that perfume the air. Newbies often share their surprise at this unexpected beauty hiding just outside Milwaukee, marveling that such pristine wilderness still exists so close to urban life. Avid outdoors-lovers praise the park’s peaceful vibe, swooning over carefree days spent alternating between woods, water, and carefree camaraderie that recharge the spirit.
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