3 day fall itinerary
Welcome to the ultimate guide for a traditional fall weekend getaway in the Elgin Area, Illinois! If you are searching for a perfect autumn escape filled with haunted history, scenic drives, and seasonal adventures, look no further. This weekend itinerary is designed to immerse you in the enchanting fall atmosphere of the Elgin Area and the spooky events that make it perfect for Halloween! From haunted houses to tranquil walks amidst vibrant fall foliage, this itinerary promises an unforgettable experience.
Day 1
Schedule
Upon arriving in the Elgin Area, Illinois, kick off your fall weekend by checking in at one of our many accommodations to immerse yourself in the autumn ambiance. You will want to get fully settled in so when you are back for the night, you are ready to settle in with your flannel pajamas.
Spend the afternoon taking a stroll through the charming Downtown Elgin Historic District, admiring the fall foliage, and exploring boutique shops. The shopping in the Elgin area is filled with unique boutiques with some gems in downtown Elgin, such as Steep and Clay, Whatnots & Whimsies, Morbid Mementos Oddities and Occult and more- you will see it filled with unique fall exclusives!
Make sure to look to see if any of the local market are running while you are in town because they are the perfect spot to pick up snacks and catch some live entertainment. Downtown Elgin Market is held every Friday from 3 p.m. to 7 p.m. in the fall. East Dundee’s Depot Market also hosts Saturday morning markets from 8 a.m. to 1 p.m. until late October. Hampshire hosts the Hampshire Farmers Market from 9 a.m. to 3 p.m. every third Saturday through October. You can find all the details about the markets here.

Day 2
Schedule

Nothing says fall morning more than grabbing a cup of coffee from a local shop. This is a great opportunity to check out the Explore Elgin Area Coffee Trail. It is free to participate in, and if you really love coffee, you could plan to visit eight (8) different participating coffee shops, then stop at the Explore Elgin Area Visitor Center to get a free mug.
No fall getaway is complete without some pumpkins some next is time to explore some area pumpkin patches. The Pumpkin Wagon in Elgin is all about decorating, painting or eating available pumpkins. This is a local favorite and was recently featured in the Enjoy Illinois Travel Guide. For an agritourism experience, head over to Enjoy Pioneer Farm to visit the animals, pick veggies and walk the patch to pick your pumpkins. If you are looking to experience everything fall in one day then head to Goebbert’s Farm – Pingree Grove. They also have veggie picking opportunities as well as the apple orchard and attractions for kids. And did someone say Pumpkin Eating Dinosaur?
This itinerary is meant to give you all of the fall feels and that is not possible without a few scares too, right? The City of Elgin’s streets have been crawling with zombies for a night of live music, food, and Halloween fun called Nightmare on Chicago Street. In late October, prepare for an evening of pulse-pounding excitement with electrifying performances, immersive environments, apocalyptic-themed drinks, delectable food options, and a soundtrack that will keep your heart racing!
Get your ticket to other events like the Fox River Trolley Museum’s Ghost Story Train and the Dark Hollows Haunted Hayride at Camp Big Timber. Plan your trip around Halloween in the Hollow for family fun and possibly a glimpse of the Headless Horseman. Not into the spooky fun, plan your visit during one of the area’s other Heritage and Fall festivals. Visit our website for a list of Fall festivals and Spooky fun at ExploreElginArea.com.
Day 3
Schedule
Spend your last day in the Elgin Area relaxing and just remembering all of the fun you have had. Set out for a scenic walk along the Fox River Trail, taking in the breathtaking fall foliage and making stops at murals, pretty views, and the smells of restaurants cooking some amazing food. In the late morning, if you’re a fan of trains and history, consider exploring the Fox River Trolley Museum for a unique experience or check out the new fall exhibit at Gail Borden Public Library. There are so many destinations along the trail so you can spend as much time as you want.
This fall itinerary offers a delightful blend of autumn charm, classic history, and outdoor exploration, ensuring a memorable spooky fall weekend in the Elgin Area! Be sure to check the availability and operating hours of attractions and restaurants in advance, especially during the bustling fall season and around city wide events. Enjoy your hauntingly delightful getaway!


