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29 Mar 2025
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7 Best Places for Weekend Trips From Davenport, IA

Weekend Getaway Itinerary Overview

Embark on an unforgettable weekend adventure with our carefully curated trip itinerary, exploring a mix of vibrant cities, charming towns, and natural wonders around the Davenport, IA area. This journey promises a blend of culture, history, and relaxation, perfect for rejuvenating the mind and spirit.

Our first stop is Chicago, IL, a bustling metropolis that offers a dynamic mix of iconic architecture, world-class museums, and diverse culinary delights. From the Art Institute of Chicago to Millennium Park, every corner has something unique to offer. Dive into its vibrant neighborhoods and experience the charming blend of cultures that the city boasts.

Next, venture to Galena, IL, a quaint town known for its well-preserved 19th-century ambiance. Stroll through its charming streets lined with delightful boutiques and visit local wineries to enjoy exquisite tastings set against the backdrop of rolling hills. This peaceful refuge is perfect for unwinding and escaping the hustle and bustle.

Outdoor enthusiasts will love Starved Rock State Park, IL, where breathtaking sandstone canyons and majestic waterfalls provide a haven for hiking, photography, and relaxation. Explore over a dozen trails, each offering spectacular views and the chance to connect with nature's splendor.

Continue the adventure in Des Moines, IA, where art meets vibrancy. Explore the Des Moines Art Center for an inspiring look at contemporary works or immerse yourself in the energetic ambiance of local farmers' markets. The city offers a perfect mix of urban life and cultural exploration.

Madison, WI, is your next stop, offering not only natural beauty with its stunning lakes, but also a lively music and arts scene that captivates visitors of all ages. Don't miss the Saturday morning farmer’s market or the scenic views from the beautiful University of Wisconsin-Madison campus.

Wind down at Lake Geneva, WI, where luxury meets natural beauty. This resort city invites you to relax by the water, explore the historic estates, and enjoy gourmet dining options in the inviting downtown area. It's the ideal spot for both adventure and tranquility.

Finally, immerse yourself in the cultural richness of Amana Colonies, IA, where history comes alive through traditional German crafts, cuisine, and cultural events. Enjoy this vibrant heritage and indulge in the artistry of local shops and festivals.

Experience a journey unlike any other that blends history, culture, nature, and relaxation for a truly enriching weekend getaway.


Recommended Activities

  • Trip Point Pin1

    Chicago, IL

    Chicago offers a vibrant mix of attractions including world-class museums, a diverse culinary scene, iconic architecture, and the bustling Navy Pier. It's a city full of cultural attractions and entertainment options, making it a perfect urban getaway.
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  • Galena is a charming historic town known for its well-preserved 19th-century buildings and scenic beauty. Enjoy a leisurely stroll through its quaint streets, explore unique shops, and indulge in the local wineries and cozy bed-and-breakfasts.
    Open Google Maps Button
  • Trip Point Pin3

    Starved Rock State Park, IL

    Starved Rock State Park is a natural treasure with stunning sandstone canyons, seasonal waterfalls, and beautiful hiking trails. It's an excellent destination for nature enthusiasts looking to explore the great outdoors and enjoy breathtaking views.
    Open Google Maps Button
  • Trip Point Pin4

    Des Moines, IA

    Des Moines is a vibrant city with a thriving arts and culture scene, featuring attractions such as the Des Moines Art Center and the impressive Pappajohn Sculpture Park. The city also boasts lively farmers' markets, unique dining experiences, and beautiful walking trails along the river.
    Open Google Maps Button
  • Trip Point Pin5

    Madison, WI

    Madison offers a perfect blend of natural beauty and urban amenities. Explore the stunning lakes, visit the renowned University of Wisconsin-Madison campus, stroll around the colorful farmers' market at Capitol Square, and take in the city's lively music and arts scene.
    Open Google Maps Button
  • Trip Point Pin6

    Lake Geneva, WI

    Lake Geneva is a scenic resort city known for its beautiful lake views, luxurious resorts, and historic estates. It's an ideal spot for relaxation, boating, and enjoying outdoor activities, as well as exploring charming shops and dining in its inviting downtown area.
    Open Google Maps Button
  • Trip Point Pin7

    Amana Colonies, IA

    Amana Colonies is a cluster of seven picturesque villages known for their rich German heritage. Visitors can explore unique artisan shops, enjoy traditional German cuisine, and experience a variety of cultural events and festivals that celebrate the area's history and craftsmanship.
    Open Google Maps Button

Restaurants

  • Restaurant Icon

    SafeHouse Milwaukee - Milwaukee, WI

    4.3
    $$$$

    SafeHouse Milwaukee - Milwaukee, WI

    This spy-themed restaurant in Milwaukee offers an immersive dining experience with secret passwords, hidden doors, and spy gadgets.
    4.3
    $$$$
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    The Chicago Diner

    4.7
    $$$$

    The Chicago Diner

    Known for its vegetarian and vegan comfort food since 1983, this iconic diner is a must-visit for unique, plant-based dining.
    4.7
    $$$$
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    The Machine Shed

    4.5
    $$$$

    The Machine Shed

    A lively restaurant themed around American farming culture, offering hearty, farm-to-table Midwestern cuisine.
    4.5
    $$$$
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    Alpine Inn

    3.7

    Alpine Inn

    Located in Rockford, IL, this quirky establishment is known for its classic American food and its unique feature of feeding leftovers to raccoons outside.
    3.7
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    Blue Star Cafe

    Blue Star Cafe

    This charming café in Amana Colonies features a menu filled with authentic German dishes and a cozy, rustic atmosphere.
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Hotels

  • Hotel Icon

    The Blackburn Inn (Virginia)

    4.5

    The Blackburn Inn (Virginia)

    A historic inn located in Staunton, VA, offering a unique blend of classic architecture and modern luxury, set amidst beautiful landscapes.
    4.5
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    The Shamrock Motel

    4.3

    The Shamrock Motel

    A nostalgic stop on the way to Wisconsin Dells, featuring bright retro decor and mid-century charm, perfect for vintage lovers.
    4.3
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    Hotel Julien Dubuque

    Hotel Julien Dubuque

    A historic hotel in Dubuque, IA, known for its timeless elegance, luxurious accommodations, and role in the city's vibrant history.
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    The Brewhouse Inn & Suites

    8.4

    The Brewhouse Inn & Suites

    Housed in a former Pabst Blue Ribbon brewery, this Milwaukee hotel offers a unique industrial-chic aesthetic with a nod to its brewing history.
    8.4
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    The Iron Horse Hotel

    8.7

    The Iron Horse Hotel

    Located in Milwaukee, this hotel caters specifically to motorcycle enthusiasts, combining modern luxury with a biker-friendly atmosphere.
    8.7
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Local Events & Happenings

  • Event Icon

    We The Kingdom

    We The Kingdom

    VIP: Early Entry and Meet & Greet and Photo with We the Kingdom. Must arrive by 5:30PM. Late arrivals will forfeit early entry seating and M&G. This event takes place in the historic Five Flags Theater, and there are no elevators to get to the mezzan...
    Map IconFive Flags Center in Dubuque (41.04 mi)
    Calendar Icon31 Aug 2025
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  • Event Icon

    Reed Timmer: Dominate the Storm

    Reed Timmer: Dominate the Storm

    Dr. Reed Timmer is an extreme meteorologist and storm chaser who specializes in intercepting the most powerful storms on the planet to collect valuable scientific data. Reed's "hands-on" experience with a vast assortment of hazardous weather and natu...
    Map IconFive Flags Center in Dubuque (41.04 mi)
    Calendar Icon7 Sep 2025
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    Gangstagrass

    Gangstagrass

    Gangstagrass is a genre-defying, multi-racial collective of musicians who blend bluegrass and hip-hop to create a unique sound that breaks down cultural and musical barriers. Known for their Emmy-nominated theme song for FX's "Justified," they've gai...
    Map IconFive Flags Center in Dubuque (41.04 mi)
    Calendar Icon14 Sep 2025
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  • Event Icon

    George Janko: MAN ON WATER TOUR

    George Janko: MAN ON WATER TOUR

    The event will take place at Five Flags Center in Dubuque.
    Map IconFive Flags Center in Dubuque (41.04 mi)
    Calendar Icon21 Sep 2025
    Picture for George Janko: MAN ON WATER TOUR
  • Event Icon

    Beatles vs. Stones - A Musical Showdown

    Beatles vs. Stones - A Musical Showdown

    The British Invasion brought us the two most popular rock groups of all time, the Beatles and the Rolling Stones, as well as the liveliest debate in rock history - which band is the greatest? These two legendary bands will engage in a musical "shoot ...
    Map IconFive Flags Center in Dubuque (41.04 mi)
    Calendar Icon26 Oct 2025
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  • Event Icon

    World Ballet Company: Nutcracker

    World Ballet Company: Nutcracker

    A Magical Holiday Adventure Awaits! Celebrate the season with The Nutcracker?a festive, family-friendly ballet full of holiday magic, whimsical characters, and Tchaikovsky?s unforgettable music to sweep you up in the moment. Featuring 40 internationa...
    Map IconFive Flags Center in Dubuque (41.04 mi)
    Calendar Icon15 Dec 2025
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    Gym Class Heroes

    Gym Class Heroes

    Travie McCoy, the charismatic frontman of gym class heroes. and a celebrated solo artist, is reinvigorating his career in 2025 with the relaunch of gym class heroes. as a solo project. Rising t o fame in the 2000s, gym class heroes. reshaped alternat...
    Map IconQ Casino Q Showroom in Dubuque (41.12 mi)
    Calendar Icon20 Sep 2025
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Travel Gems from Reddit

  • Reddit Icon

    15 votes, 34 comments. What are some of your favorite long weekend getaways that are nearby? Wife and I would like to take a quick trip. Up for

    Weekend getaway

    15 votes, 34 comments. What are some of your favorite long weekend getaways that are nearby? Wife and I would like to take a quick trip. Up for

    /r/desmoines
  • Reddit Icon

    43 votes, 48 comments. Not sure this is the best place to ask, but here it goes. What are the best places to vacation for a long weekend in and

    Vacation in and around Iowa

    43 votes, 48 comments. Not sure this is the best place to ask, but here it goes. What are the best places to vacation for a long weekend in and

    /r/Iowa
  • Reddit Icon

    East: Places like the Warren Dunes ... of road trip/camping style places as well as some nice towns to visit like Saugatuck and Holland. West, Galena is railroad/mining town r...

    Recommendations for long weekend within 2-3 hours of Chicago in October?

    East: Places like the Warren Dunes ... of road trip/camping style places as well as some nice towns to visit like Saugatuck and Holland. West, Galena is railroad/mining town r...

    /r/ChicagoSuburbs
  • Reddit Icon

    40 votes, 158 comments. Planning on spending a 3-day weekend with a buddy of mine in Quad Cities at Hotel Blackhawk. We are from Chicago and doing a

    Tips for a 3-day weekend in QC?

    40 votes, 158 comments. Planning on spending a 3-day weekend with a buddy of mine in Quad Cities at Hotel Blackhawk. We are from Chicago and doing a

    /r/QuadCities
  • Reddit Icon

    14 votes, 28 comments. We moved to the Quad Cities a few years ago and have done a lot of what is offered around here. I'd love to know your day

    Day trips from the Quad Cities

    14 votes, 28 comments. We moved to the Quad Cities a few years ago and have done a lot of what is offered around here. I'd love to know your day

    /r/QuadCities

Music for Your Journey

  • Music Icon

    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    An upbeat classic that celebrates the joy of traveling and the open road.
    Listen on Spotify
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  • Music Icon

    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    A quintessential travel anthem that's perfect for any road trip playlist.
    Listen on Spotify
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    WALK THE MOON - Shut Up and Dance

    WALK THE MOON - Shut Up and Dance

    An energizing and fun song that keeps spirits high during long drives.
    Listen on Spotify
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    Rusted Root - Send Me on My Way

    Rusted Root - Send Me on My Way

    An uplifting track with a laid-back vibe, ideal for leisurely road trips.
    Listen on Spotify
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    Adele - Hometown Glory

    Adele - Hometown Glory

    A comforting song about belonging and finding joy in the journey.
    Listen on Spotify
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  • Music Icon

    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A laid-back tune that encourages relaxation and taking life as it comes.
    Listen on Spotify
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  • Music Icon

    Coldplay - Adventure of a Lifetime

    Coldplay - Adventure of a Lifetime

    An inspiring song with an upbeat tempo, perfect for exploring new places.
    Listen on Spotify
    Picture for Coldplay - Adventure of a Lifetime
  • Music Icon

    Vance Joy - Riptide

    Vance Joy - Riptide

    A catchy and feel-good song with a summery vibe, great for road trips.
    Listen on Spotify
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  • Music Icon

    Don McLean - American Pie

    Don McLean - American Pie

    A nostalgic and iconic song that provides a narrative for the trip.
    Listen on Spotify
    Picture for Don McLean - American Pie
  • Music Icon

    Black Eyed Peas - I Gotta Feeling

    Black Eyed Peas - I Gotta Feeling

    An energetic track that sets a positive mood for any travel adventure.
    Listen on Spotify
    Picture for Black Eyed Peas - I Gotta Feeling