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15 Best Things to Do in Freeport (IL)

A county seat and city of around 24,000, Freeport is couched in the rolling Northwest Illinois countryside.

The population grew suddenly from the 1850s when Freeport became a base for manufacturing. Many of the settlers at this time were German, and Freeport soon became known as “Pretzel City, USA” thanks to a popular bakery founded in 1869.

This heritage is remembered more than 150 years later, and a pretzel is even the mascot for Freeport High School.

In 1858 downtown Freeport hosted the second Lincoln-Douglas Debate, which had lasting repercussions for the 1860 presidential election and the ensuing Civil War.

You can visit the site of this debate and dive into Freeport’s rich culture and past at attractions like the Stephenson County Historical Society Museum and the vibrant Freeport Art Museum.

1. Stephenson County Historical Society Museum and Arboretum

The history of Freeport and Stephenson County comes alive at this riveting museum, couched in a charming three-acre arboretum with specimen trees and gardens.

The center of attention on this campus is the 1857 Taylor House, thought to have been part of the Underground Railroad during the Civil War.

The house is built from rusticated, locally quarried limestone and belonged to Oscar Taylor who was the son of a Speaker of the House of Representatives, and opened Freeport’s first bank.

The basement is believed to have been a hiding place for fugitive slaves, and a secret door for this purpose is still intact in the basement.

There’s much more to check out on the grounds, like an historic schoolhouse, a museum preserving industrial artifacts, a museum for the cast-iron Arcade toys manufactured in Freeport and a log cabin dating to the mid-19th century.

2. Lincoln-Douglas Debate Square

In 1858 a seismic historical event happened in downtown Freeport. Here, the second of seven debates took place between Abraham Lincoln and incumbent Stephen Douglas in the run up to the United States Senate elections.

Slavery was the most prominent topic, and it was in this debate that Douglas articulated his Freeport Doctrine.

This damaged his standing in the South and ultimately split the Democratic Party, paving the way for his defeat (and Lincoln’s Victory) in the later Presidential Election in 1860.

The site of the debate has interpretive waysides explaining this momentous event, as well as a lifesize monument of the two men, installed in 1992.

3. Krape Park

This refined, award-winning park is on the banks of Yellow Creek, southwest of downtown Freeport.

Set in century-old woodland, Krape Park has some striking features, like a 44-foot waterfall tumbling down a limestone cliff and an elegant white bridge from 1919.

In summer you can rent a canoe or paddle boat for a trip along the creek, and by the water is the Yellow Creek Adventure Golf Course, open Memorial Day weekend through September.

The Koenig Amphitheatre stages outdoor concerts and festivals throughout the season, and in September is an anchor for Art in Park, brimming with art booths and live music.

Some of the wealth of other attractions at Krape Park include a unique vintage carousel, an 18-hole disc golf course, tennis courts and sledding hills and cross-country ski trails in winter.

4. Freeport Art Museum (FAM)

The Freeport-based industrialist William Thomas Rawleigh (1870-1951) traveled the world and amassed a diverse art collection with the purpose of bringing the world to the doorstep of his hometown.

That collection formed the basis for the Freeport Art Museum, founded in 1975 and housed in a palatial former school building from 1911.

FAM hosts important traveling exhibitions and curates its own shows, drawing from its impressive collection spanning 4,000 years.

There’s something new to see every eight to ten weeks at the Ferguson and Newell Galleries, while there’s a gallery upstairs for work by talented local solo artists, groups and students. The museum is community oriented, with dynamic public programs for all ages.

5. Read Park

A recreation honeypot, Read Park is full of sports and leisure amenities for all ages. This is the home of the Freeport Park District administration office, and the park’s pavilion hosts many park district programs, like painting, Tai Chi and martial arts.

Within the park’s boundaries is Freeport’s premier skate park, as well as the Read Park Family Aquatic Center, offering a large zero-depth pool, slides, spray features and more.

Close to the pavilion are softball fields, basketball courts and a children’s playground, while there’s a set of tennis courts on the south side along Empire Street.

On the southwest corner is the remarkable Little Cubs Field, a one-third size replica of Wrigley Field, even featuring ivy, bricks, dirt and sod from the original stadium.

Available for rental, this field is used mostly for little league games, but you also take a look around for free and admire the attention to detail.

6. Union Dairy

When the cherished Union Dairy opened in 1914, Stephenson County had more creameries than anywhere else in Illinois.

The dairy gained its name through a merger or union with a rival dairy. Then in 1934, after moving to its current location on the Lincoln-Douglas Debate Square, Union Dairy started to produce the ice cream that would make it famous.

The parlor has always been known for its innovation, and the popular Orange Pudding is one wacky flavor that has made it through to the present.

The menu is bursting with tempting treats, from sundaes to surprising scoop combinations, shakes and cakes, and also serves all beef Chicago-style hot dogs, sandwiches, burgers and a big choice of sides.

7. Jane Addams Recreation Trail

With gentle rolling hills, prairie, oak woods, creeks and wetlands, the countryside in Freeport’s backyard deserves some exploration.

A great way to do this is on the 17-mile Jane Addams Recreation Trail, named for the Nobel Prize-winning political activist and reformer, who was born close by in Cedarville in 1860.

You can pick up the trail at Tutty’s Crossing Trailhead in downtown Freeport and head off on a memorable journey north to the Wisconsin border where the path merges with the 40-mile Badger Trail, extending to Madison, WI.

You’ll never be far from a watercourse on the route, and there are 22 bridges to cross, like the Van Buren Bridge (1885) on the Pecatonica River, and a charming old covered bridge outside Orangeville.

8. Silver Creek & Stephenson Railroad & Museum

An enthralling piece of railroad history has been preserved just south of Freeport. Here you can experience steam branch-line railroad on a 3.4-mile stretch of track along the former Milwaukee Road, pulling away from the Silver Creek Depot.

Drawing a set of historic cabooses along this track is a 36-ton Heisler steam locomotive. If this is out of order, the museum also has a fleet of more modern diesel alternatives.

Every few months there are seasonal rides down the track, like the spooky Train of Terror in October.

Close by is the Silver Creek History Museum, on the site of a large former poorhouse from 1902, turned into a sheltered care home later in the 20th century.

You’ve got 28 rooms of local history to browse, and the most impressive exhibit is a 130-ton stationary engine still in working order.

9. Park Hills Golf Course

This highly rated public golf facility has two 18-hole courses in an idyllic undulating landscape. Both courses are relatively short, but with some unforgiving rough so you’ll need to be precise and think carefully about risk vs reward on these tracks.

True to its name, Park Hills has hilly terrain to contend with, especially on the West Course (slope rating of 121), which has six or so uphill holes that play a club longer.

You can practice your swing at the 300-yard driving range, which has natural grass tees and 15 hitting stations, while the pro shop stocks any piece of equipment you might be missing.

10. Oakdale Nature Preserve

The Freeport Park District manages this calming slice of nature, outside the city around five miles south of downtown.

On 133 acres, the Oakdale Nature Preserve blends forests, stream habitats and prairie. Being away from the city, the preserve is never crowded and has four miles of trails for hiking, dog walking and bicycling, as well as a ⅓-mile accessible trail.

You’ll find interpretive signs along the trails, along with a picnic area and fire pit.

11. Wishful Acres Farm & Brewery

About ten miles out into the gently rolling Northwest Illinois countryside is a small-batch brewery operating on a family farm.

The farm grows more than 100 varieties of vegetables, fruits, herbs, micro-greens, hops and garden plants, all pre-sold via its CSA program.

The craft brewery was founded here in 2016 and has a taproom and bar on-site where you can sample 12 on draft and choose your favorites to take home in 22-oz bottles and growlers.

The beer list changes by the week and well over 100 different varieties have been produced since the brewery opened. Where possible the ingredients, from hops to flavorings, are grown right here on the farm.

12. Children’s Hands-On Museum of Northwest Illinois

At the Freeport Lincoln Mall there’s a great children’s museum with more than 6,000 feet of interactive space in a labyrinthine building.

The ever-changing exhibits help children and families explore, learn and create through interactivity. The museum handles subjects like science, technology, engineering and math (STEM), social sciences, art, drama and music.

Children can also roleplay professions and everyday situations, at a restaurant, medical clinic, farm and more. There are two rooms especially designed for tots, as well as a sensory room for children with disabilities.

13. Taylor Park

The land for the original park of the Freeport Park District was acquired as long ago as 1905. On Freeport’s northeast shoulder, Taylor Park is the third-largest in the city, and harks back to a horse track used for trotting races.

The completely flat terrain is a holdover from that time, as is the roughly oval trail encircling many of the park’s sports amenities.

Taylor Park’s three lighted softball fields host the Park District’s highly competitive adult leagues and tournaments, and there are also tennis courts, basketball courts, a concession stand, a statue of Lincoln from 1929 and a picnic shelter.

14. Winneshiek Playhouse

Established in 1916, the Winneshiek Players is thought to be the oldest continuously operating amateur theater company in the country.

The company has produced a season of performances every year, since 1926 and moved to its current location downtown in 1936.

This venue has been updated over the years, with extensions in the 1940s and remodeling in the 60s and 80s.

Holding audiences of up to 216, the Winneshiek Playhouse is a fine place to watch the company’s plays and musicals, selected to appeal to all tastes.

Recent productions have included the Rocky Horror Picture Show, Leading Ladies (Ken Ludwig), Witness for the Prosecution and Six Dance Lessons in Six Weeks (Richard Alfieri).

15. Stephenson County Visitor Center

Strategically located a few miles out of Freeport on Highway 20, this visitor center is a useful introduction to Stephenson County and its many attractions and amenities.

The welcoming and knowledgeable staff will be happy to provide directions and information about local history, tours and guides, accommodations, restaurants and the many activities available in the county.

There’s also a shop at the center stocking locally made gifts, from artisan cosmetics to t-shirts, jewelry and handmade Christmas decorations.

15 Best Things to Do in Freeport (IL):

• Stephenson County Historical Society Museum and Arboretum
• Lincoln-Douglas Debate Square
• Freeport Art Museum (FAM)
• Union Dairy
• Jane Addams Recreation Trail
• Silver Creek & Stephenson Railroad & Museum
• Park Hills Golf Course
• Oakdale Nature Preserve
• Wishful Acres Farm & Brewery
• Children’s Hands-On Museum of Northwest Illinois
• Taylor Park
• Winneshiek Playhouse
• Stephenson County Visitor Center

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Free & Cheap Things to Do in Freeport, IL

• The list below includes 30 free or cheap things to do in or near Freeport, Illinois, including 47 different types of inexpensive activities like Bowling, Art Museum, Parks and Walking Trails.
• From Krape City Park to Jane Addams Recreation Trail, there are a variety of budget-friendly attractions in Freeport and in nearby cities within 25 miles like Monroe , Rockford , Oregon and New Glarus .

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Krape city park, jane addams recreation trail, oakdale park, lincoln douglas debate square, little cubs field, oscar taylor home, oakdale nature preserve, freeport arts center, freeport art museum, sk8 park in reed park.

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Looking for something to do this weekend in the Freeport area? Here are 12 upcoming events

Cedar fest 2024.

What: Cedar Feast 2024 features Wesley Loring playing Friday night and Free Fall playing Saturday Night after the fireworks show.

When: 11 a.m. Friday, June 28 to 2 a.m. Sunday, June 30

Where: The Cedar Inn, 4747 Illinois Route 26 N, Cedarville

Swiftie Camp

What: Does your athlete love Taylor Swift? Then this camp is for them. This camp is for athletes of all ability levels. All attending athletes should plan to bring a lunch and a water bottle. During camp there will be morning tumbling instructional time, Taylor Swift themed craft time, lunch break, afternoon tumbling instructional time and Swiftie themed games/activities.

When: 9 a.m. to 3 p.m. Friday, June 28

Where: Pierce Athletics, 916 S. Arcade Ave., Freeport

Cost: $55; $40 for members

What: This fundraiser for the Northern Illinois Dyslexia Center and the Freeport Elks Lodge includes dinner and live music by The Soft Shoe Shufflers. Dinners served from 4:30-7 p.m.

When: 4 to 7 p.m. Saturday, June 29

Where: Elks Lodge, 608 W. Stephenson St., Freeport

The Real Deal

What: The Real Deal performs R&B along with a variety of old school and new school, for your listening and dancing pleasure.

When: 7 p.m. Saturday, June 29

Where: Best Dam Bar, 13965 Best Road, Davis

Yankee Doodle Bash

What: This Independence Day extravaganza features games, food and drinks, face painting, temporary tattoos and fireworks show. For the whole family.

When: 5 to 8 p.m. Saturday, June 29

Where: Cedarville Community Center, 430 W. Washington St., Cedarville

Pretzel City 5K

What: The course consists of flat roadways and paths that wind through Krape Park. The Pretzel City 5K is a Rockford Road Runners circuit race. Register online or on race day starting at 7 a.m.

When: 8 a.m. Saturday, June 29

Where: Krape Park, 1799 S. Park Blvd., Freeport

Cost: $35; $15 for age 19 and younger

Bummyfest 2024

What: The 19th annual Bummyfest block party fundraiser includes live music by Lola Blue (country) and The Beaux Band (rock), beer, food trucks, live auction, 50/50 and other raffles. The  Pink Heals Stephenson County  pink firetruck will also be on site. All proceeds go to charity. Bring your chairs and favorite beverages if you're picky about what we provide. All donations welcome.

When: 4 p.m. to 1 a.m. Saturday, June 29

Where: 204 W. South St., Pearl City

Peach Farm Direct Truckload Sale

What: Sweet and Juicy Freestone peaches will be available, as well as Elliott pecans. There are no purchase limits and everyone is welcome. Bring cash, checks, Apple Pay or major credit card.

When: 10 to 11:30 a.m. Saturday, June 29

Where: Stephenson County Fairgrounds, 2250 S. Walnut Road, Freeport

What: Hometown gig for the hometown kid.

When: 3 to 6 p.m. Sunday, June 30

Where: Coach's Golf & Grill, 621 W Lena St, Lena

Music in the Park

What: Dan, Deb and Dewey will share country, acoustic folk and bluegrass tunes. Bring a lawn chair, grab a treat at the Snack Shop and enjoy the tunes. For music lovers of all ages. In case of inclement weather, the concert will be moved to St. John's Lutheran Church, 625 Country Lane Drive; signs will be posted at the park.

When: 6 p.m. Sunday, June 30

Where: Lions Park, 609 N. Schuyler St., Lena

Cost: Free admission

Sunday Funday Music

What: Original artists perform in the taproom on Sundays. The Danny Project performs June 30.

When: 2 to 5 p.m. Sunday, June 30

Where: Lena Brewing Co., 9416 Wagner Road, Lena

Concert in the Park

What: Enjoy performances from the Freeport Concert Band at the iconic band shell under a canopy of trees. There is bench seating available or bring lawn chairs.

When: 7 p.m. Sunday, June 30

Where: Koenig Amphitheater, Krape Park, 1 Park Blvd., Freeport

Coming next week

Solar printing.

What: Solar printing on special paper. Bring feathers, leaves, other items with cool shapes, or use materials provided. Use these images as art or make a unique card. Event is for adults/teens/older children with a guardian. 

When: 11:30 a.m. to 1:30 p.m. Tuesday, July 2

Where: Meeting Room, Freeport Public Library, 100 E. Douglas St., Freeport

Footloose in Scotland

What: "Footloose in Scotland" is Johnny Lynn's 400+ miles of walking through the lowlands and highlands, along lochs and through glens, etc. with lots of photos and stories to result. Take an adventure to Scotland with Johnny Lynn. No registration required.

When: 6:30 to 7:30 p.m. Tuesday, July 2

This article originally appeared on Rockford Register Star: Looking for something to do this weekend in the Freeport area? Here are 12 upcoming events

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Freeport and Stephenson County host numerous events each year to enliven the spirt of the area, showcase our greatest attractions and welcome visitors to experience the best of our region.

Upcoming annual events.

The Jimmys Concert – April 6, 2024

Purchase tickets by clicking here. 

Stephenson County Home Show – April 20, 2024

Do you have your eye on a home remodeling or landscaping project this season? Come meet with contractors and suppliers all in one space! The Stephenson County Home Show returns to the Stephenson County Fairgrounds, Saturday April 20 from 10 am to 4 pm. Visit with professionals in several service industries to tackle your next home project knowing you’re in good hands. See you for the Home Show on April 20.

Pretzel Fest – April 27, 2024

Join us for Downtown Freeport’s second annual Pretzel Fest! Living in Pretzel City, whether you are a graduate or a local resident, the pretzel is honored and revered. In celebration of National Pretzel Day on April 27, we are hosting the best Pretzel Fest the salty snack has ever seen! Activities include a BBQ competition, performances, and more! Pretzel Fest will also be an opportunity to enjoy the Downtown Freeport Festival District – purchase your alcoholic beverage from participating restaurants/bars and carry it with you through the downtown festivities! Dozens of boutiques, shops, and restaurants offer pretzel merchandise and food options to celebrate your favorite salty snack.

Pretzel City Winefest – May 11, 2024

Wine enthusiasts from around the region flock to Downtown Freeport to enjoy great shopping, food and, of course, wine at Pretzel City Winefest!

Get your tickets here!

Wineries and wine retailers from around the region are showcased at participating storefronts in Downtown Freeport where attendees can walk around and try their favorite varieties while shopping a variety of locations they may miss on a normal trip to downtown. Pretzel City Winefest is hosted by the Greater Freeport Partnership to attract residents and visitors to downtown businesses and showcase the wonderful shops and restaurants Freeport offers.

A $25 general admission ticket includes souvenir tasting glass, wine bag and tasting hours noon – 4 pm. We will also provide you with a booklet and map of the 16 participating locations in Downtown Freeport!

Music on Chicago – June 7, July 5, August 2

Music on Chicago has been a tradition in Downtown Freeport for over 20 years because of the great music, comradery, and summer-celebration atmosphere it brings! All events take place in Downtown Freeport’s new Art Plaza at the corner of Chicago Avenue and Douglas Street. The grounds are ideal for a social gathering with friends or bring the family and blankets to take your spot on the lawn. This year’s entertainment includes: June 7 – In the Stix w/DJ Cup July 5 – Harlan Jefferson & Mimi on the Mic August 2 – Boogie & the Yo-Yoz w/DJ Cup

$5 admission includes access to the summer’s best party and entertainment by amazing musical acts. Local food vendors are available for dinner options and volunteers serve alcoholic and non-alcoholic beverages during the event. Come join the fun in 2023!

Pretzel City Brewfest – September 28, 2024

BUY TICKETS HERE!

The BEST EVENT in ILLINOIS is back! Bring your friends and enjoy the best beer-tasting event in the region! Sample beers direct from the breweries of the area in a lively event format featuring food trucks and competitive games.  This is a 21 and older event that takes place rain or shine.

Participants can purchase $40 general admission ticket online which includes entry, 20 tasting tickets, and a souvenir glass. There will be a  limited number of $75 VIP passes also available, which include one-hour early entry, 30 tasting tickets, access to special releases, a Brewfest t-shirt, a special VIP souvenir glass, swag bag, and VIP lounge.

Tickets can be purchased in advance with credit/debit card online. Tickets will also be available at the gate for $40 for general admission the day of the event, VIP will not be sold the day of the event. Designated driver tickets can be purchased the day of the event at the gate for $10.

All of this year’s Brewfest information can be found on the Greater Freeport Partnership mobile app. Download it for free on Google Play Store or Apple App Store for a listing of breweries attending, special releases, food vendors and other important event details.

Arctic Ale & Art Walk – February 24, 2024

By the end of February we are all ready to get out of the house and break the cabin fever! Arctic Ale & Art Walk is your cure for the winter blues and entice you into Downtown Freeport for a sampling of local beer, shopping and exhibits by local artists and artisans all while enjoying your favorite downtown stores. Live music fills the streets at warming stations throughout downtown as you stroll during this Freeport Festival District day (link to City’s Festival District page). This is a FREE event, however please start your day by checking in to receive your tasting wristband and cup at the corner of Stephenson Street and Chicago Avenue from noon to 4 pm.

For more information, visit the event Facebook page

Key Industries

Construction, plumbing, heating, & service, private label food manufacturing, calendar feed.