The Ultimate Chicago to Holland Road Trip Itinerary
Cruise from Windy City vibes to Dutch delights on this Lake Michigan adventure, exploring hidden gems and iconic sights along the shore.
You're cruising along the eastern shore of Lake Michigan, the windows down, and the fresh lake breeze tousling your hair. To your left, golden beaches stretch as far as the eye can see, punctuated by towering sand dunes and charming lakeside towns. To your right, lush forests and rolling farmlands paint a picturesque Midwest landscape. This, my fellow road trippers, is the magic of the Chicago to Holland route – a journey that takes you from the bustling urban energy of the Windy City to the quaint Dutch charm of Holland, Michigan.
As a seasoned road tripper and current adventure tour operator, I've driven this route more times than I can count. Each time, I discover something new – a hidden beach, a quirky roadside attraction, or a mouthwatering local delicacy. This 150-mile adventure isn't just about getting from point A to point B; it's about savoring every mile of the journey, embracing the unexpected, and immersing yourself in the diverse cultures and landscapes of the Midwest.
So, buckle up, crank up your favorite road trip playlist, and get ready to explore the ultimate Chicago to Holland road trip. From urban landscapes to serene lakeshores, from world-class museums to windmills and wooden shoes, this trip offers a little bit of everything. Let's hit the road!
Hike the Indiana Dunes National Park
Just an hour's drive from Chicago, Indiana Dunes National Park feels like a world away from the city's hustle and bustle. As you crest the first dune, the vastness of Lake Michigan stretches before you, a mesmerizing blue expanse that seems to touch the horizon. The park's 15,000 acres offer a diverse playground for nature lovers, with hiking trails winding through dunes, wetlands, prairies, and forests.
Don't miss the 3 Dune Challenge, a heart-pumping hike that takes you up the park's three tallest sand dunes. It's a workout, but the panoramic views from the top are worth every step. After your hike, cool off with a dip in the refreshing waters of Lake Michigan at West Beach.
Key Information:
- Location: 1215 N State Road 49, Porter, IN 46304
- Best Time to Visit: Early morning for cooler temperatures and fewer crowds
- Duration: 3-4 hours
Why Stop Here: Experience a unique ecosystem where forest meets beach, with rare plants, diverse wildlife, and stunning lake views.
Road Tripper's Tip: Pack a picnic and enjoy it at the Dune Ridge Trail overlook for breathtaking sunset views over the lake.
Explore New Buffalo's Charming Downtown
As you cross into Michigan, the charming town of New Buffalo welcomes you with open arms. This quintessential beach town offers a perfect blend of lakeside relaxation and small-town charm. Stroll down Whittaker Street, the town's main drag, lined with unique boutiques, art galleries, and inviting cafes.
Make your way to the New Buffalo City Beach, where you can sink your toes into the soft sand and watch sailboats glide across the horizon. If you're feeling adventurous, rent a kayak or paddleboard to explore the calm waters of the Galien River, which flows into Lake Michigan.
Key Information:
- Location: Downtown New Buffalo, MI 49117
- Best Time to Visit: Late afternoon to evening for a pleasant stroll and dinner
- Duration: 2-3 hours
Why Stop Here: Experience the laid-back vibe of a classic Michigan beach town with great dining and shopping options.
Road Tripper's Tip: Try the legendary burgers at Redamak's, a local institution since 1975.
Climb the Dunes at Warren Dunes State Park
Prepare to be awestruck by the massive sand dunes at Warren Dunes State Park. Rising 260 feet above Lake Michigan, these natural wonders offer a unique blend of challenging climbs and exhilarating views. As you scale Tower Hill, the park's highest dune, you'll feel like you're climbing a mountain of sand.
Once you reach the top, catch your breath and take in the sweeping views of the lake and surrounding forests. For an adrenaline rush, try dune surfing – sliding down the steep sandy slopes on a sandboard or toboggan. It's an experience that will have you laughing and covered in sand in equal measure.
Key Information:
- Location: 12032 Red Arrow Highway, Sawyer, MI 49125
- Best Time to Visit: Early morning for cooler sand and fewer crowds
- Duration: 2-3 hours
Why Stop Here: Conquer some of the most impressive sand dunes in the Midwest and enjoy three miles of pristine beach.
Road Tripper's Tip: Bring sturdy shoes for climbing and a change of clothes – you'll be finding sand in unexpected places for days!
Ride the Silver Beach Carousel in St. Joseph
Step back in time at the Silver Beach Carousel in St. Joseph. This meticulously restored 1910 carousel is a whimsical wonder that delights visitors of all ages. As you mount one of the 48 hand-carved horses or chariots, the calliope music transports you to a bygone era of simple pleasures and childhood joy.
After your ride, explore the nearby Silver Beach with its soft sand and picturesque lighthouse. Don't miss the splash pad on hot summer days – it's a hit with kids and kids-at-heart alike.
Key Information:
- Location: 333 Broad St, St Joseph, MI 49085
- Best Time to Visit: Afternoon, especially on weekends when the carousel is in full swing
- Duration: 1-2 hours
Why Stop Here: Relive childhood memories and create new ones on this beautifully restored piece of Americana.
Road Tripper's Tip: For a special treat, time your visit with one of the carousel's evening rides, when the thousands of lights create a magical atmosphere.
Sample Local Wines at Fenn Valley Vineyards
As you continue north, the landscape shifts to rolling hills dotted with vineyards. Make a stop at Fenn Valley Vineyards, where you can sample award-winning wines crafted from locally grown grapes. The winery's location, just a few miles from Lake Michigan, creates a unique microclimate perfect for grape cultivation.
Take a guided tour of the vineyards and wine cellar to learn about the winemaking process, from vine to bottle. Then, settle in for a tasting flight on the outdoor patio, surrounded by lush grapevines. Don't miss their signature Riesling, which perfectly captures the terroir of Michigan wine country.
Key Information:
- Location: 6130 122nd Ave, Fennville, MI 49408
- Best Time to Visit: Early afternoon for tours and tastings
- Duration: 2-3 hours
Why Stop Here: Discover Michigan's burgeoning wine scene and enjoy tastings with beautiful vineyard views.
Road Tripper's Tip: Designate a driver or consider booking a local wine tour to fully enjoy the tasting experience responsibly.
Visit the South Haven Lighthouse
The charming maritime town of South Haven is home to one of the most photographed lighthouses on Lake Michigan. The South Haven Lighthouse, with its bright red exterior, stands sentinel at the end of a long pier jutting into the lake. Walk the pier for an up-close view of this historic beacon, which has guided sailors safely to shore since 1903.
After admiring the lighthouse, explore South Haven's quaint downtown, filled with unique shops and waterfront restaurants. If you're visiting in August, you might catch the National Blueberry Festival, celebrating the region's bountiful blueberry harvest.
Key Information:
- Location: 355 Water St, South Haven, MI 49090
- Best Time to Visit: Late afternoon for the best lighting for photos
- Duration: 1-2 hours
Why Stop Here: Capture iconic lighthouse photos and experience a quintessential Lake Michigan harbor town.
Road Tripper's Tip: For the best views of the lighthouse, take a sunset cruise on a replica tall ship from the Michigan Maritime Museum.
Paddle the Kalamazoo River in Saugatuck
Saugatuck, often called the "Art Coast of Michigan," offers a perfect blend of natural beauty and cultural charm. One of the best ways to experience the town's scenic beauty is by paddling the Kalamazoo River. Rent a kayak or canoe and meander through the calm waters, surrounded by lush forests and occasional glimpses of charming waterfront homes.
As you paddle, keep an eye out for local wildlife – herons, turtles, and even the occasional bald eagle are known to frequent the area. The river eventually opens up into Lake Kalamazoo, offering stunning views of the town's harbor and the famous Mount Baldhead sand dune.
Key Information:
- Location: Saugatuck, MI 49453 (various rental locations available)
- Best Time to Visit: Morning for calm waters and wildlife sightings
- Duration: 2-3 hours
Why Stop Here: Experience the natural beauty of Michigan's waterways and get a unique perspective on Saugatuck.
Road Tripper's Tip: Pack a waterproof bag for your camera to capture the scenery without worrying about splashes.
Ride the Chain Ferry in Saugatuck
For a unique transportation experience, hop aboard the Saugatuck Chain Ferry. This hand-cranked ferry, one of the last of its kind in the country, has been shuttling passengers across the Kalamazoo River since 1838. As you glide across the river, propelled by the rhythmic turning of the ferry operator's crank, you'll feel like you've stepped back in time.
The short ride offers beautiful views of Saugatuck's waterfront and is a fun way to access Oval Beach on the other side. It's more than just a means of crossing the river – it's a cherished piece of local history and a delightful experience in itself.
Key Information:
- Location: 730 Water St, Saugatuck, MI 49453
- Best Time to Visit: Mid-day when the ferry runs most frequently
- Duration: 5-10 minutes for the ride, allow extra time for potential wait
Why Stop Here: Experience a unique mode of transportation and a piece of living history.
Road Tripper's Tip: Have some cash ready for the small fare – credit cards aren't accepted on the ferry.
Sunbathe at Oval Beach in Saugatuck
Consistently ranked as one of the best beaches in the United States, Oval Beach is a must-visit stop on your road trip. As you crest the dunes and catch your first glimpse of the vast expanse of golden sand and blue water, you'll understand why this beach has earned its accolades.
The clean, soft sand is perfect for sunbathing, beach games, or building sandcastles. Take a refreshing dip in Lake Michigan's clear waters, or simply stroll along the shoreline, collecting beach glass and watching the sailboats on the horizon. The beach's west-facing orientation makes it an ideal spot to catch a spectacular Lake Michigan sunset.
Key Information:
- Location: Oval Beach Dr, Saugatuck, MI 49453
- Best Time to Visit: Late afternoon for swimming and staying for sunset
- Duration: 2-4 hours
Why Stop Here: Experience one of the Midwest's most beautiful beaches and witness a stunning Lake Michigan sunset.
Road Tripper's Tip: Arrive early to secure parking, especially on summer weekends when the beach can get crowded.
Explore the Saugatuck Dunes State Park
For a more secluded beach experience, head to Saugatuck Dunes State Park. This pristine natural area boasts 2.5 miles of shoreline and towering sand dunes that reach up to 200 feet high. The park's hiking trails wind through diverse ecosystems, from hardwood forests to open dunes, offering a chance to explore Michigan's unique coastal environment.
Take the Beach Trail for a moderate 2.5-mile round trip hike that rewards you with a secluded stretch of Lake Michigan shoreline. Along the way, you might spot some of the park's abundant wildlife, including deer, foxes, and a variety of bird species.
Key Information:
- Location: 6575 138th Ave, Holland, MI 49423
- Best Time to Visit: Morning for cooler hiking temperatures and fewer people on the trails
- Duration: 3-4 hours
Why Stop Here: Experience a wilder side of Lake Michigan with pristine dunes and secluded beaches.
Road Tripper's Tip: Bring plenty of water and wear sturdy shoes – the sandy trails can be challenging in spots.
Tour the Historic Felt Mansion
Tucked away in the woods near Saugatuck, the Felt Mansion offers a glimpse into the opulent lifestyle of the early 20th century. Built in the late 1920s by self-made millionaire Dorr Felt, this summer home boasts 25 rooms and stunning architectural details. As you tour the mansion, you'll learn about the Felt family's history and the property's various incarnations over the years – from a Catholic seminary to a state police post.
Don't miss the chance to climb the mansion's tower for panoramic views of the surrounding Saugatuck Dunes State Park and Lake Michigan in the distance. The beautifully restored gardens are perfect for a leisurely stroll after your tour.
Key Information:
- Location: 6597 138th Ave, Holland, MI 49423
- Best Time to Visit: Afternoons for guided tours (check schedule in advance)
- Duration: 1-2 hours
Why Stop Here: Step back in time and experience the grandeur of a bygone era in a beautifully restored mansion.
Road Tripper's Tip: Combine your visit with a hike in the adjacent Saugatuck Dunes State Park for a perfect blend of history and nature.
Visit Nelis' Dutch Village in Holland
As you approach Holland, embrace the town's Dutch heritage at Nelis' Dutch Village. This theme park offers a charming recreation of life in the Netherlands during the 1800s. Wander through the village's canals and gardens, admiring the traditional Dutch architecture and colorful tulip beds.
Watch artisans demonstrate traditional Dutch crafts like wooden shoe carving and Delftware painting. Don't miss the folk dancing performances, complete with authentic costumes. For a taste of Dutch cuisine, try some fresh-made stroopwafels or poffertjes (mini pancakes) at one of the village's eateries.
Key Information:
- Location: 12350 James St, Holland, MI 49424
- Best Time to Visit: Mid-morning to catch most of the demonstrations and performances
- Duration: 2-3 hours
Why Stop Here: Immerse yourself in Dutch culture and history in a fun, interactive setting.
Road Tripper's Tip: Visit during the week for smaller crowds and more personal interactions with the village's artisans.
Explore Windmill Island Gardens
No visit to Holland is complete without seeing DeZwaan, the only authentic Dutch windmill in the United States. Standing tall at Windmill Island Gardens, this 250-year-old working windmill was brought over from the Netherlands and reassembled here. Climb to the top for panoramic views of Holland and watch the miller grind wheat into flour using traditional methods.
The surrounding gardens are a riot of color during the spring tulip season, but they're beautiful year-round with manicured beds and winding canals. Don't miss the Amsterdam street organ demonstrations or the hand-painted Dutch carousel.
Key Information:
- Location: 1 Lincoln Ave, Holland, MI 49423
- Best Time to Visit: Spring for tulips, but beautiful in all seasons
- Duration: 2-3 hours
Why Stop Here: See a piece of authentic Dutch history and enjoy stunning gardens in the heart of Holland.
Road Tripper's Tip: Time your visit for one of the daily windmill tours to learn about its fascinating history and operation.
Stroll Downtown Holland
End your road trip with a leisurely stroll through downtown Holland. This vibrant district perfectly blends Dutch heritage with modern Midwest charm. Brick-paved streets lined with unique shops, art galleries, and cozy cafes invite exploration. Don't miss the twice-weekly farmers market (Wednesdays and Saturdays) for fresh local produce and artisanal goods.
For a unique experience, visit during the winter months when the downtown sidewalks are heated, keeping them snow and ice-free – a nod to Holland's innovative spirit. Stop by New Holland Brewing for a taste of local craft beer and farm-to-table cuisine.
Key Information:
- Location: 8th Street, Holland, MI 49423
- Best Time to Visit: Evening for dinner and a stroll
- Duration: 2-3 hours
Why Stop Here: Experience the perfect blend of Dutch heritage and modern Midwest charm in a vibrant downtown setting.
Road Tripper's Tip: Check the city's event calendar for festivals and street performances that often enliven the downtown area.
Relax at Holland State Park Beach
Cap off your journey with a visit to Holland State Park Beach, home to Holland's iconic "Big Red" lighthouse. This expansive sandy beach offers plenty of space for sunbathing, beach games, or simply relaxing with a good book. The shallow waters near the shore are perfect for swimming and wading.
As the day winds down, find a spot on the beach to watch the sun set behind the lighthouse. The vibrant colors reflecting off Lake Michigan and silhouetting Big Red create a postcard-perfect end to your Chicago to Holland road trip.
Key Information:
- Location: 2215 Ottawa Beach Rd, Holland, MI 49424
- Best Time to Visit: Late afternoon through sunset
- Duration: 2-3 hours
Why Stop Here: Experience one of Michigan's best beaches and see the famous Big Red lighthouse.
Road Tripper's Tip: Bring a picnic dinner to enjoy on the beach as you watch the sunset.
Your Day-by-Day Chicago to Holland Road Trip Adventure
Now that we've explored the highlights of the route, let's put it all together into a perfectly paced itinerary. Remember, road trips are all about flexibility, so feel free to adjust this plan to suit your interests and travel style.
Day 1: Chicago to New Buffalo
Start your journey early to beat Chicago traffic. Head east on I-90, then south on I-94 into Indiana.
- Morning: Hike the Indiana Dunes National Park (2-3 hours)
- Lunch: Grab a quick bite at the park or pack a picnic
- Afternoon: Continue to New Buffalo, Michigan (1-hour drive)
- Evening: Explore New Buffalo's downtown and enjoy dinner at a local restaurant
- Overnight: Stay in New Buffalo
Driving time: Approximately 2 hours (70 miles)
Day 2: New Buffalo to South Haven
- Morning: Start with breakfast in New Buffalo, then head to Warren Dunes State Park (30-minute drive)
- Late Morning: Climb the dunes at Warren Dunes State Park (2-3 hours)
- Lunch: Picnic at the park or grab a bite in nearby Sawyer
- Afternoon: Drive to St. Joseph (30 minutes) and visit the Silver Beach Carousel
- Late Afternoon: Continue to South Haven (35-minute drive)
- Evening: Watch the sunset at South Haven Lighthouse, dinner in town
- Overnight: Stay in South Haven
Driving time: Approximately 1 hour 15 minutes (65 miles)
Day 3: South Haven to Saugatuck
- Morning: Start with a South Haven beach walk, then drive to Fennville (30 minutes)
- Late Morning: Wine tasting at Fenn Valley Vineyards (2 hours)
- Lunch: Enjoy a picnic with your newly purchased wine and local treats
- Afternoon: Drive to Saugatuck (15 minutes), paddle the Kalamazoo River (2-3 hours)
- Evening: Explore Saugatuck's downtown, dinner at a waterfront restaurant
- Overnight: Stay in Saugatuck
Driving time: Approximately 45 minutes (35 miles)
Day 4: Saugatuck
Spend a full day exploring the charms of Saugatuck.
- Morning: Take the Chain Ferry to Oval Beach for a morning beach walk
- Late Morning: Hike in Saugatuck Dunes State Park (2-3 hours)
- Lunch: Picnic in the park or head back to town for a local café
- Afternoon: Tour the Felt Mansion (1-2 hours)
- Evening: Art gallery hopping in downtown Saugatuck, dinner in town
- Overnight: Stay in Saugatuck
Driving time: Minimal, mostly local
Day 5: Saugatuck to Holland
- Morning: Final stroll through Saugatuck, then drive to Holland (15 minutes)
- Late Morning: Visit Nelis' Dutch Village (2-3 hours)
- Lunch: Try Dutch treats at the village
- Afternoon: Explore Windmill Island Gardens (2-3 hours)
- Evening: Stroll downtown Holland, dinner at New Holland Brewing
- Overnight: Stay in Holland
Driving time: Approximately 15 minutes (15 miles)
Day 6: Holland
Spend your final day soaking up the Dutch charm of Holland.
- Morning: Visit Holland Farmers Market (if it's Wednesday or Saturday)
- Late Morning: Beach time at Holland State Park
- Lunch: Picnic at the beach or try a local lakeside restaurant
- Afternoon: Relax on the beach or rent bikes to explore Holland's bike paths
- Evening: Farewell dinner in downtown Holland, sunset at Big Red Lighthouse
- Overnight: Stay in Holland
Driving time: Minimal, mostly local
This itinerary offers a perfect blend of outdoor adventures, cultural experiences, and relaxation. It allows you to savor each stop along the route without feeling rushed. Remember, the joy of a road trip lies in the journey itself, so don't hesitate to make unexpected stops or detours along the way. Happy travels!
Practical Tips for Your Chicago to Holland Road Trip
To help you make the most of your journey, here are some road-tested tips:
- Timing is Everything: Plan your trip for late spring through early fall for the best weather and open attractions. May is ideal for Holland's famous Tulip Time Festival, while July and August offer perfect beach weather.
- Pack Smart: Bring layers for unpredictable Lake Michigan weather, beach gear, comfortable hiking shoes, and a good camera to capture the memories.
- Stay Connected: Download offline maps before your trip, as cell service can be spotty in some rural areas.
- Fuel Up: Gas stations are plentiful along the route, but it's always wise to fill up when you're at half a tank.
- Beach Essentials: Pack sunscreen, insect repellent, and a beach umbrella for shade during long days by the lake.
- Taste Local: Try regional specialties like Michigan cherries, lake perch, and locally brewed craft beers.
- Avoid Traffic: Start your journey early to beat Chicago traffic, especially if leaving on a Friday.
- Flexible Planning: While having an itinerary is great, allow for spontaneous stops – some of the best memories come from unexpected discoveries.
- State Park Pass: Consider purchasing a Michigan State Park Pass if you plan to visit multiple state parks along the route.
- Water Safety: Always heed beach warning flags and be aware of rip currents in Lake Michigan.
- Parking Prep: Bring quarters for parking meters in beach towns, especially during peak season.
- Eco-Friendly Travel: Bring reusable water bottles and shopping bags to minimize waste on your trip.
- Local Events: Check town websites for local events happening during your visit – you might stumble upon a fun festival or concert.
- Early Bird Gets the Worm: Start your days early, especially for popular attractions, to beat the crowds and make the most of your time.
- Sunset Chasing: Plan to be at a westward-facing beach at least once during your trip for a spectacular Lake Michigan sunset.
Conclusion: Your Lake Michigan Adventure Awaits
From the towering skyscrapers of Chicago to the charming windmills of Holland, this road trip along Lake Michigan's eastern shore offers a little bit of everything. You'll experience the natural wonders of towering sand dunes and pristine beaches, the cultural richness of Dutch heritage and artistic communities, and the warm hospitality of Midwest lake towns.
As you drive north, you'll feel the pace of life slow down, inviting you to savor each moment of your journey. Whether you're climbing dunes, sampling local wines, or watching the sun set over Lake Michigan, each day brings new adventures and memories to cherish.
Remember, the real magic of a road trip often happens between destinations – in the conversations had, the roadside stands discovered, and the unexpected detours taken. So while this itinerary serves as a guide, don't be afraid to go off-script and create your own unique adventure.
As you roll into Holland, with windmills on the horizon and the scent of tulips in the air, you'll realize that the journey from Chicago has been more than just a drive – it's been a voyage through the heart of Lake Michigan culture. So pack your bags, hit the road, and get ready for an unforgettable Midwest adventure. The lakeshore is calling, and it's time to answer!
West Parker, a Cornell University School of Hotel Administration graduate, has spent two decades as the secret weapon of the jet-set elite, crafting bespoke adventures that redefine luxury travel. Now a resident writer for Town & Tourist, this 45-year-old "Architect of Extraordinary Journeys" combines razor-sharp insights with unparalleled industry connections to deliver experiences that even the most discerning globetrotters can't help but rave about. West's expertise spans from exclusive real estate to fine dining, making him the go-to strategist for those who demand nothing but the extraordinary in their travels.
