Fall Date Ideas in Bloomington, Illinois

2023 Fall Date Ideas in Central Illinois  

The leaves are about to change! That means new opportunities for date night ideas that only fall weather can bring. We’ve pulled together some of the best Bloomington-Normal date ideas for couples to try.  

And we encourage you to turn these date nights into overnights for an added special effect. Check our availability and plan an epic date night getaway. Whether it’s “just because” or an anniversary, show your love this fall. Every day is a day worth celebrating, and the perfect excuse to create your next significant memory… no matter the season you’re in.  

Our Top 5 Autumn List of Activities

  1. Go for a hike to see the changing leaves and fall foliage 
  2. S’mores by the fire but upgraded!
  3. Free Outdoor Concerts in Normal, IL
  4. Festivals and Farms for Oktoberfest, Pumpkins and Apples 
  5. Patio Dining based on your favorite food and drinks 

Go for an Illinois Hike to see the Fall Foliage  

Walk through the woods to see the changing leaves together, and take pictures with your favorite trees as the backdrop. Hiking is a cheap date idea that can turn into a memorable adventure when you talk about the moments from this year that you’re thankful for and the moments you’re looking forward to.  

The following spots are within a 45-minute drive of Bloomington. (Previous guest tip… download the free version of the All Trails app. It will help you find where to park, read reviews of the trails, and keep you ON the trail, too!)  

hiking trail covered in fall leaves along the left side of a creek

Upgrade your S’Mores by the Fire  

You’re an adult now, so that means you can upgrade your s’mores game. A tip from a previous guest… don’t get standard chocolate bars. Instead, get those little individually wrapped Ghirardelli chocolate squares that are already the perfect shape… and you can get them filled with caramel, raspberry, mint and other flavors. Unwrap them and put them near the fire so when your marshmallows are ready and you start to assemble the perfect s’more, the chocolate has softened just the right amount. It’s a cute date idea that could turn into a messy one, so remember the napkins!  

Don’t have a fire pit? We’ve got an outdoor fireplace, and a S’mores by the Fire for 2 package you can add on to your overnight stay for $15. (Add it to your room at online checkout)  

outdoor fireplace next to a brick path and a garden

2023 Free Outdoor Fall Concerts in Normal, Illinois  

The days are occasionally still muggy, but nights can be perfect when you LoungeAbout the Roundabout in Uptown Normal. (Located at the circle by the Amtrak train station.) Check out these completely free September concerts. Bring a folding chair and relax. 

View the Uptown Normal website to see the times and learn more about the artists!

  • 08/30/23 Christina Eltrevoog at Uptown Circle
  • 09/01/23 emily the band – LIVE @ Uptown Circle
  • 09/02/23 Nicotine Poetic – LIVE @ Uptown Circle
  • 09/06/23 Grant Milliren – LIVE @ Uptown Circle
  • 09/07/23 John Till – LIVE @ Uptown Circle
  • 09/08/23 The Neals – LIVE @ Uptown Circle
  • 09/09/23 James Herr – LIVE @ Uptown Circle
  • 09/13/23 Inktrail – LIVE @ Uptown Circle
  • 09/16/23 Shuga Beatz – LIVE @ Uptown Circle
  • 09/20/23 Kate Herald – LIVE @ Uptown Circle
  • 09/27/23 Kickin’ & Pickin’ – LIVE @ Uptown Circle

2023 Festivals & Farms in Central Illinois  

Get your fair food on and dive into the hyper focused world of thematic festivals. Apples. Pork. Beer. Oktoberfest. It’s fall ya’ll. 

Or allow yourself to be kids again and check out a local pumpkin farm! Go with the one you love, take a hay ride and laugh. Get lost in a corn maze. Pick the perfect pumpkins, take them home and carve them, and then proudly display your new artwork on your front porch. There are two pumpkin farms near Bloomington-Normal. Take a leisurely drive and sip homemade apple cider on your way back.  

  • Rader Family Farms is open Sept. 9-Oct. 29, 2023 for their fall activities. $20.95 for admission, $10 for those 65+, and free for veterans, active military and children under 4.  
  • Tanner’s Orchard is north of Peoria in Speer, Illinois. They feature an apple orchard, pumpkin patch, wagon rides and a corn maze. Their pumpkin donuts and apple cider is something you’ll definitely want to take home with you.  

Patio Dining at Locally Owned Bloomington, IL Restaurants  

The following restaurants in town have ideal outdoor patios, perfect for a date night. Here are some guest favorites to help you find your spot, whether you prefer a casual night out or a romantic date idea.  And remember that downtown Bloomington is a 15-minute walk from the mansion, so when you turn date night into an overnight, you can walk back to the mansion afterward and relax (maybe with some s’mores!)  

  • Wine & Tapas – Mystic Kitchen & Tasting Room. They have the best by-the-glass selection and charcuterie boards in Bloomington. Not to mention creative shareable flatbreads and amazing entrée specials. Every Thursday and Friday they have wine tasting hours from 6-9pm.  
  • Farm to Table – Epiphany Farms. If you’re looking for fresh seasonal local ingredients, paired with stellar cocktails… this is your spot. And they have the best fall soups. If the Squash Velouté is available, get it and thank us.  
  • Side of History – Rosie’s Pub is located in Abraham Lincoln’s former law office, with one of the most beautiful bars in Bloomington. Everything on their menu is fantastic, but locals rave about their creative salads and some of the best burgers around. And if you’ve never had their Lobster fettuccini, you’re missing out.  
  • BBQ & Bourbon – Brass Pig Smoke & Alehouse. Illinois might not have the bourbon trail, but Brass Pig has some of the most unique selections of bourbons and whiskeys in town. Their Whiskey Wednesday special might be perfect for you. And their BBQ options span salads, sandwiches and plates of smoked meat goodness. Get the curly fries. Trust us. 
  • Pizza & Beer – Flingers Pizza Pub. Try one of their craft pizzas, customized Flinger Rolls, or a Cheesebomb. But don’t forget to try one of their 24+ different beers on tap, with several from local brewers. Anything is available as a 5oz so you can find your favorite to pair with dinner under the pergola. 
  • Pet Friendly – Lil Beaver Brewing has a newly expanded menu and a spacious outdoor patio area that is dog friendly. They brew their own really unique beers with flavor combinations you’d never guess. Grab a patio table by the outdoor fire pit and a flight of beers this fall.   

view of McLean County Museum through orange and yellow mum flowers

Turn Date Night into an Overnight at Vrooman Mansion  

Whether it’s an anniversary or you just wanted an excuse to say “I love you,” fall is the perfect time to plan a date night that extends into an epic gourmet breakfast the next morning.  

Skip the hotel and choose to stay in a mansion. Built in 1869, we preserve its vibrant character and history, and blend it with the modern amenities you need. Pick one of our 7 rooms that best fit your personality. Then enjoy s’mores by the fire after your night on the town. The next morning we’ll serve you a gourmet breakfast in our dining room or (if the morning weather is perfect for you) we can serve you on the outdoor patio.  

Significant moments have always happened here. Choose us as your next historic landmark, and come make history. Book today. 

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