Romantic Weekend Getaways Midwest

Augusta, Missouri

Points of Interest: Wineries
Best time to Visit: Fall – Spring

Augusta, Missouri, is a romantic getaway if you love wineries. 

The small wine town in Missouri makes for a perfect weekend getaway with the one you love. 

The wine town is tucked into the rolling hillside allowing for scenic views of grassy hills and treelines for as far as the eye can see.

While here, make sure to check out the Augusta Wine Trail. The Wine Trail consists of 5 different wineries. [Read also: Wineries in Augusta

The list of wineries are listed below:

  • Augusta Winery
  • Balducci Vineyards
  • Montelle Winery
  • Noboleis Vineyards
  • Mount Pleasant Estates

Kelleys Island, Ohio

Points of Interest: Geological Preserve, State Park, Island 
Kelley’s Island, Ohio, is a great place to explore with the ones you love.

The island features Kelleys Island State Park, which has over 676 acres to explore. Make sure to rent a Kayak and explore Lake Erie. 

If the conditions are right, you can even kayak to the 2-mile-long Starve Island. 

The park also features a swimming beach and hiking trails. With so much to do, it is easy to spend an entire day at Kelleys Island State Park exploring the great outdoors.

Another great attraction around Kelley’s Island is the famous Glacier Grooves, a geological preserve with outlines from Glacier Grooves from over 18,000 years ago and marine fossils dated from 350-400 million years ago. 

These are just a few of the many different attractions offered at Kelley’s Island. [Read also: Best Kellys Island Attractions]

Grafton, Illinois

Points of Interest: Wineries | Small Town

Grafton, Illinois, offers the perfect romantic weekend getaway.

Grafton has a charming small town that is great for grabbing a bite to eat and enjoying a glass of wine next to the Mississippi River. 

While in the Grafton downtown, stop by one of the antique, boutique, or ice cream shops. Making it a great way to spend the day supporting small businesses.

Another great aspect of what makes Grafton, Illinois, the perfect weekend getaway is the romantic wineries throughout the winding roads. 

Atop the hill, you will find Aeries Winery, which offers fantastic views of the Mississippi River. 

It is a great way to relax, sip on wine and enjoy the company of those around you!

Chesterton, Indiana

Points of Interest: Beaches
Best time to Visit: Summer

The Indiana Dunes National Park in Chesterton, Indiana, is another Romantic Destination in the Midwest. 

The national park is a great place to explore over 15,000 acres with sandy shorelines and over 50 miles of hiking trails

Therefore, making it a great place to discover.

However, what makes this such a romantic weekend getaway is the ability to take a walk along the sandy beaches during sunset and enjoy the beach-style lakefront. 

With vast waters surrounding the shoreline, it is easy to forget you are actually on a lake, not an ocean. [Read also: Guide to Visiting the Indiana Sand Dunes

In addition to the Indiana Dunes National Park, there are over nine different beaches to explore in the area. Beaches include:

  • Dunbar Beach
  • Indiana Sand Dunes State Park
  • Kemil Beach
  • Lake View Beach
  • West Beach
  • Porter Beach
  • Portage Lakefront and Riverwalk
  • Central Avenue Beach
  • Mount Baldy Beach
The sandy beaches and beautiful beach-style lakefront is the reason Chesterton, Indiana, made our list of Top Romantic Weekend Destinations in the Midwest. 

Red Wing, Minnesota

Points of Interest: Small Charming Town, Local Eats and Boutiques, Outdoor

Red Wing, Minnesota, is a beautiful and charming town located off the Mississippi River. 

Red Wing includes a variety of breweries and wineries for those looking to have a drink while relaxing. 

The lovely small town also features local eats and boutiques, making your dining and shopping experience unique.

While here, try outdoor activities, including hiking, biking, boating, and golfing. These are a few outdoor activities offered in Red Wing, Minnesota.

However, what makes this a romantic getaway is the small picturesque town with vast and beautiful bluff views that will make you want to come back for more. 

The small-town charm and scenic views are the reason it made our list of Top Romantic Weekend Destinations in the Midwest.

Empire Beach, Michigan

Points of Interest: Beaches

Best time to Visit: Summer

Empire, Michigan, is a small beach town that offers an enchanting vibe

The small town features beautiful views of beaches, soaring bluffs, and sandy dunes.

Empire, Michigan, is the home of Sleep Bear Dunes National Lakeshore. The lakeshore offers a breathtakingly beautiful destination that has sandy beaches and dunes.

Empire, Michigan, is a great place to escape with loved one to make memories for years to come.

Gelena, Illinois

Points of Interest: Small Town, Shopping, Wineries

Best time to Visit: Winter

Galena, Illinois, is a perfect destination to spend the weekend with the love of your life. The quaint downtown features over 125 businesses along the 1800’s style buildings that give a romantic appearance, especially during winter.

In addition to the charming town, Galena features various wineries to enjoy

Wineries are located throughout downtown Galena and the rolling countryside, allowing for picturesque views of scenic backdrops while sipping wine-[Read also: Wineries in Galena IL].

Another significant aspect is the town’s unique businesses, which include locally owned coffee shops, homemade chocolates, and custom craft shops that allow you to take in the small-town culture that comes with it.

The charming, quaint town is filled with wine, and local shops make it a must-visit destination for any couple looking to get away from the daily grind—[Read also: Reasons to Visit Galena, Illinois].

Full List of Top Romantic Weekend Destinations in the Midwest

  1. Augusta, Missouri
  2. Kelleys Island, Ohio
  3. Grafton, Illinois
  4. Chesterton, Indiana
  5. Red Wing, Minnesota
  6. Empire Beach, Michigan
  7. Galena, Illinois
Romantic Weekend Getaways Midwest

About Author, Sara Elizabeth
Writer, Amora V Lifestyle
Co-Owner of

Sara is a writer for Amora V Lifestyle and is Co-Owner of Amora V Boutique. Sara previously worked as a Marketing Manager and has her Master’s from Lindenwood University.

Sara studies everything of interest, from psychology, recipes, finances, mental health, and travel, thriving to find happiness and to live a good life.

When not learning, Sara loves all things outdoors, food, and hanging around great company. Furthermore, Sara loves spending time with family, who she is blessed to have in her life.

Note from the author: Through my articles, I hope to bring you joy and peace and that you enjoy it!

Disclaimer: The views and opinions expressed in this artcile are solely those of the author and do not necessarily represent those of any organizations mentioned or affiliated with. The information provided in this blog is accurate and up-to-date to the best of the author’s knowledge, but readers are advised to do their own research and confirm any information before making travel plans or decisions. The author is not responsible for any loss, injury, or inconvenience sustained by readers while traveling based on the information provided in this blog. Travel at your own risk and always prioritize your safety and well-being. Any reviews or comments written are the subjective opinion of an Amora V Lifestyle member and not Amora V Lifestyle. Amora V Lifestyle performs occasional checks on commentary left by users. It’s worth mentioning that we may also use comments in our articles. By posting a comment, you are giving us permission to use it in our content. Please check out Privacy Policy and Terms of Use for full disclosure. 


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