Midwest Getaways: Small Towns, Scenic Routes, and Surprising Adventures

When people think of travel, the Midwest isn’t always the first place that comes to mind, but it deserves a spot on the list. From charming small towns and peaceful lakeside escapes to quiet forest trails and quirky roadside finds, this region is full of the kind of places that surprise you in the best way.

I’ve lived in the Midwest most of my life, and even after exploring destinations around the world, I keep coming back to the beauty and variety found right here. There’s something grounding about these close-to-home getaways, easy to reach, rich in character, and often overlooked.

This blog is an evolving collection of Midwest destinations worth visiting, revisiting, and sharing. Whether you're planning a quick weekend escape or looking for inspiration for your next road trip, you'll find ideas, tips, and personal favorites here, with more added all the time.

Shawnee Forest Country, Illinois

Quick Look
Distance from Chicago: 5.5 hours
Best for: Nature lovers, wine weekends, low-key outdoor escapes
Best time to visit: Fall or spring
Top picks: Canoeing in the Cache River, local vineyards, forest hikes

Why Visit
Tucked into the southern tip of Illinois, Shawnee Forest Country feels like an entirely different side of the state. With quiet hiking trails, lush forests, and one of the most unique wetland ecosystems in the Midwest, it’s a destination that balances adventure with total stillness. Add in local wineries and scenic drives, and it’s an ideal unplugged weekend away.

Top Things to Do

• Cache Bayou Outfitters: Rent a canoe or kayak and explore the cypress-filled Cache River, one of the most biodiverse spots in the region

• Shawnee Hills Wine Trail: Stop at standout wineries like Blue Sky Vineyard, known for its Tuscan-style tasting room and sweeping views, Alto Vineyards, one of Illinois’ oldest and most awarded wineries, and StarView Vineyards, a relaxed spot with great live music and lakefront seating

• Hike Rim Rock Trail or Bell Smith Springs: Scenic trails with natural bridges, bluffs, and shaded paths through the forest

Erin’s Notes
What I love most about this area is how slow everything feels, in the best way. It’s the kind of place where you sip wine without rushing, paddle past ancient trees, and actually hear yourself think. The scenery here is underrated, the people are welcoming, and the mix of outdoor and wine country energy makes for a perfectly balanced trip.

Don’t Miss This Shot
A still shot of the cypress trees reflecting in the Cache River during golden hour

Indiana Dunes, Indiana

Quick Look
Distance from Chicago: 1 hour
Best for: Beach days, easy hikes, nature within reach
Best time to visit: Summer or early fall
Top picks: West Beach, Cowles Bog Trail, Dune Succession Trail

Why Visit
Indiana Dunes is one of those places that surprises people, especially when they realize it’s just an hour outside of the city. Towering sand dunes meet the shoreline of Lake Michigan, where you can climb a trail and then dip your toes in the water minutes later. But beyond the obvious beach appeal, the park also protects some of the most diverse ecosystems in the Midwest: wetlands, black oak savannas, and prairie, all layered into one.

Top Things to Do

• West Beach: Hike the Dune Succession Trail loop, then relax on the shore

• Cowles Bog Trail: A moderate hike through wetlands and woods that opens up to the beach

• Sunset views over Lake Michigan: Pack a blanket and stay for the colors

Erin’s Notes
I always forget how wild this place feels until I’m back, the towering sand, the lake breeze, the quiet moments when you feel like you’re somewhere far from the Midwest. It’s one of my favorite easy resets when I need nature without going far.

Don’t Miss This Shot
The boardwalk trail through Cowles Bog at golden hour

Chicago, Illinois

Quick Look
Best for: Urban explorers, culture seekers, creative energy
Best time to visit: April through October
Top picks: Lakefront walks, neighborhood architecture, vibrant arts, and food

Why Visit
Chicago isn’t just a city; it’s a mosaic of neighborhoods, lakefronts, skylines, and stories. It’s a place where you can start your morning kayaking on the river, spend the afternoon exploring a Mexican mural project in Pilsen, and end the night listening to live jazz in a tucked-away club. The lakefront trail stretches for miles and connects beach scenes to skyscraper views to quiet parks, making this one of the most walkable and livable big cities in the U.S.

Top Things to Do

• Stroll or bike the Lakefront Trail from Grant Park to Montrose Beach

• Explore neighborhood gems like the Garfield Park Conservatory, the National Museum of Mexican Art, or Andersonville’s indie shops

• Take an architecture tour, but skip the touristy versions and opt for one by the Chicago Architecture Center or a neighborhood walking tour

Erin’s Notes
As someone who calls Chicago home, I never run out of things to love here. It’s the contrast that keeps me inspired, serene lake mornings followed by loud, creative energy in the city’s streets. And the neighborhoods? Each feels like its own city entirely. If you want to feel the real pulse of Chicago, start there.

Don’t Miss This Shot
The skyline reflected in the water by North Avenue Beach or Promontory Point

Milwaukee, Wisconsin

Quick Look
Distance from Chicago: 1.5 hours
Best for: Culture without crowds, local breweries, lakefront energy
Best time to visit: Summer or fall
Top picks: RiverWalk, Milwaukee Art Museum, Third Ward

Why Visit
Milwaukee feels approachable in a way that bigger cities often don’t. There’s a balance here between history and creative momentum, where revitalized warehouses host artists and taprooms, and where old-world architecture blends with a growing modern identity. Set along Lake Michigan’s edge, the city offers bikeable waterfront trails, food-forward neighborhoods, and a sense of discovery if you’re into off-the-radar cities with a lot to say.

Top Things to Do

• Walk or bike the RiverWalk, lined with murals, cafés, and brewpubs

• Spend time in the Historic Third Ward, full of galleries, boutiques, and loft-style restaurants

• Visit the Milwaukee Art Museum, not just for the exhibits, but for the architecture and lake views

Erin’s Notes
I think of Milwaukee as the Midwest’s best-kept city secret. It doesn’t shout for attention, but the more time you give it, the more it gives back. The arts scene is strong, the lakefront is peaceful, and there’s something about the energy here that feels both relaxed and buzzing.

Don’t Miss This Shot
The Milwaukee Art Museum’s winged architecture against the lake

Lake Geneva, Wisconsin

Quick Look
Distance from Chicago: 90 minutes
Best for: Slow weekends, lakefront strolls, historic charm
Best time to visit: Late spring through fall
Top picks: Lake Shore Path, downtown shops, sunset cruises

Why Visit
Lake Geneva combines old-money elegance with relaxed Midwest charm. It has all the trappings of a classic lake town: boats, ice cream stands, and porch rockers, but it also offers winding lakefront paths past 19th-century estates, nostalgic steamboat cruises, and a walkable town filled with galleries and antique shops.

Top Things to Do

• Walk a stretch of the Lake Shore Path and admire the Gilded Age mansions

• Take a boat cruise at sunset, some still run on historic steam engines

• Explore local shops, grab coffee, and wander without a plan

Erin’s Notes
It’s a place where time slows down, and that’s the whole point. I’ve visited Lake Geneva many times, but nothing beats the golden light on the water in late summer when the town is lively but not overcrowded.

Don’t Miss This Shot
Looking back at the lake from the path near Black Point Estate

New Buffalo, Michigan

Quick Look
Distance from Chicago: 90 minutes
Best for: Beach days, casual wine weekends, summer escapes
Best time to visit: Late spring through early fall
Top picks: New Buffalo Beach, local wineries, downtown food scene

Why Visit
Tucked into Michigan’s southwest corner, New Buffalo is where small-town lake vibes meet weekend luxury. You’ll find sandy beaches, charming restaurants, cozy wine bars, and the kind of boutiques that make you want to browse for hours. It’s an easy and reliable summer escape that doesn’t require overplanning.

Top Things to Do

• Swim or watch the sunset at New Buffalo Beach

• Explore the local food scene, from lobster rolls to seasonal cocktails

• Visit nearby wineries like Round Barn or Gravity for tastings with a view

Erin’s Notes
There’s something about New Buffalo that feels instantly relaxing. Maybe it’s the fresh air, or maybe it’s that everything is close enough to walk to. It’s a summer staple for a reason, but even in the shoulder seasons, it holds on to its charm.

Don’t Miss This Shot
The sun dipping into Lake Michigan behind the marina

Minneapolis, Minnesota

Quick Look
Distance from Chicago: 6 to 7 hours
Best for: Creative energy, nature in the city, vibrant food scene
Best time to visit: Late spring through early fall
Top picks: Chain of Lakes, North Loop, Sculpture Garden

Why Visit
Minneapolis is a city of contrasts: lakes and lofts, bikes and bookstores, breweries and bold art. It’s a place where you can kayak in the morning and see a contemporary dance performance at night, or spend hours in a coffee shop before hitting the trails. Its creative heart is matched by its outdoorsy soul, and it feels equal parts dynamic and grounding.

Top Things to Do

• Walk, bike, or paddle around the Chain of Lakes

• Explore the North Loop for vintage shops, small batch roasters, and indie boutiques

• Visit the Walker Art Center and adjacent Sculpture Garden

Erin’s Notes
Minneapolis might be the most underrated city I’ve visited in the Midwest. The culture scene is strong, from live music to experimental art, and it has this calm, clean, easy-to-navigate layout that makes exploring effortless. It’s one of those places you could visit for a weekend and start imagining what it’d be like to move there.

Don’t Miss This Shot
The Spoonbridge and Cherry sculpture with the skyline peeking behind it