Galena Country Fair Weekend 2027
Columbus Day Weekend · Grant Park, Galena
October 9–10, 2027
The fair is Saturday, October 9 and Sunday, October 10, 2027, in Grant Park. Below: the details that matter for planning, how we’d handle parking, and Galena vacation homes for Friday, October 8 through Monday, October 11.
Search homes for Oct. 8–11 Fair details42.3934° N 90.3258° W · Galena, IL
When is the Galena Country Fair in 2027? Saturday, October 9 and Sunday, October 10, 2027, in Grant Park at 625 Park Avenue, across the Galena River from downtown Galena. The fair is held every year on Columbus Day weekend and has more than 100 hand-selected art, craft and fine-art vendors, volunteer-run food and drink, and live music. It happens rain or shine, pets are not allowed, and entry has been a $3 suggested donation at the gate.
- Oct. 9–10, 2027Sat & Sun, Columbus Day weekend
- 100+ vendorsHandmade art, craft & fine art
- $3 suggestedDonation at the gate (2026)
- Free shuttleFrom three remote lots
- No petsService dogs only
- Rain or shineNo rain date
The organizer has confirmed the 2027 dates. Hours, admission, parking and shuttle details below are from the 2026 fair and are labeled that way until the 2027 details are posted. Last checked September 29, 2026.
Coming to this year’s fair? The 2026 Galena Country Fair is Saturday, October 10 and Sunday, October 11, 2026. See homes for October 9–12, 2026.
01 · The facts
2027 Galena Country Fair at a glance
| Dates | Saturday, October 9 and Sunday, October 10, 2027 |
|---|---|
| Hours | 2027 hours not yet posted. In 2026: Saturday 10 a.m. to 5 p.m., Sunday 10 a.m. to 4 p.m. |
| Location | Grant Park, 625 Park Avenue, Galena, IL 61036 (east side of the Galena River) |
| Admission | $3 suggested donation at the gate in 2026. Proceeds support nonprofits in Jo Daviess County. |
| Parking | Free remote lots with a free shuttle. Limited paid parking at the city lot near the Old Train Depot, 91 Bouthillier St. |
| Shuttle | In 2026: every 30 minutes, 8 a.m. to 6 p.m. both days, between the remote lots and Green Street Plaza near City Hall. Free; donation boxes on board. |
| Pets | Not allowed. Only trained service dogs may enter Grant Park during the fair; emotional support animals are not permitted. |
| Weather | Rain or shine. No rain date and no indoor location. |
| Run by | The all-volunteer Galena Country Fair Planning Committee, raising funds for Jo Daviess County Country Fair Charities, Inc. |
Official source: galenacountryfair.com. Check it for final hours and shuttle times before you go.
02 · Stay with us
Galena vacation homes for Country Fair weekend
The search starts with Friday, October 8 to Monday, October 11, 2027. Change the dates, guests or bedrooms right in the search. Homes and rates come straight from our booking calendar, so what you see is what can be booked right now.
Booking for Country Fair 2027 opens October 11, 2026. We take reservations up to 365 days ahead, so our calendars open for these dates then. Until then, the search below covers our current open dates, or email us at rentals@thecollectionvacationhomes.com and we’ll let you know when the weekend opens.
Country Fair weekend carries a 3-night minimum. If nothing fits, try a Thursday arrival or email us; we know which homes are a good match for which groups.
03 · The fair
What the Country Fair is, and why people stay the weekend
This is an arts-and-crafts fair, not a carnival. There are no rides. Grant Park fills with tents from more than 100 vendors selling home decor, seasonal pieces, jewelry, clothing, toys, photography and fine art. Vendors apply in the spring and are hand-selected by the fair committee, with the focus on original, handmade work.
The food matters as much as the shopping. The fair runs its own stands: Vittle House (pork chop sandwiches, brats, chili, hot cider), Grab ’n Go (walking tacos, baked potatoes) and the Gazebo Garden, which pours Galena Cellars wine and sangria near the live music. Other booths add hand-cut fries, fudge, craft beer and cocktails. (Menu details are from 2026.)
The fair has been running for more than forty years. Since 2003, more than $1 million raised there has gone back into Jo Daviess County through grants and donations to local nonprofits, and hundreds of local volunteers work it each year. The $3 at the gate stays here.
The fair itself is a few hours. What makes it a weekend is everything around it: Main Street, the wineries, the U.S. Grant Home, and a Monday holiday for a lot of people. Because it is one of Galena’s busiest fall weekends, it also makes sense to be here already on Friday night rather than driving in with the Saturday crowd.
Who Country Fair weekend suits
- Shoppers and gift buyers. With 100-plus handmade vendors in one park, it’s an easy place to get a head start on holiday gifts.
- Families with kids. There is a children’s games area and the park playground, plus a silent auction and raffle. If you’re bringing a stroller, see the note on the bridge stairs below.
- Groups of friends and extended family. Easy to split up at the fair and meet back at the house.
- Good to know: the fair doesn’t allow pets, so four-legged travelers will enjoy the weekend from the house. And since this is one of Galena’s busier fall weekends, if you’re hoping for a quieter visit, another October weekend may suit you better.
04 · The weekend
A realistic Friday-to-Monday plan
- Arrive Fri, Oct. 8, 2027
- Depart Mon, Oct. 11, 2027
- 3 nights
Friday: arrive and settle in
Check-in is 4 p.m. Pick up groceries on the way. Downtown restaurants are busy all weekend, so book Friday dinner ahead or plan to cook at the house.
Saturday: the fair, early
Get to a shuttle lot before gates open (10 a.m. in 2026). Two to four hours is enough for most people. Spend the afternoon on Main Street, or head back to the house before the evening dinner rush.
Sunday: the rest of Galena
Tour the U.S. Grant Home, stop at a winery, or take a fall drive. Sunday also works for the fair if you’d rather flip the two days; it has closed an hour earlier than Saturday.
Monday: an easy trip home
Checkout is 11 a.m. Monday is Columbus Day, so if you have it off, you skip the Sunday-afternoon traffic leaving town.
Early October is often when the hills around Galena start to turn. Peak color changes year to year, so treat it as a bonus rather than the reason for the dates.
05 · Getting there
Country Fair parking, the shuttle and the walk in
Grant Park is on the east bank of the Galena River, across the pedestrian bridge from downtown. Parking near the park is very limited that weekend, and the intersection of Park Avenue and Highway 20 is closed. This is how it worked in 2026:
- Park freeWalmart, Galena High School or the Alice T. Virtue Pool lot
- Ride the shuttleEvery 30 minutes, 8 a.m. to 6 p.m. (2026). Free; donations welcome
- Green Street PlazaDrop-off near City Hall, 101 Green St., downtown
- Walk the footbridgeOver the Galena River to Grant Park. Stairs at both ends
Free remote lots and shuttle
- Walmart, 10000 Bartel Blvd. (shuttle loads near the gas station)
- Galena High School, 1206 N. Franklin St. (upper, northwest lot)
- Alice T. Virtue Pool, 1811 Field St. (first lot on the right, by the pickleball courts)
- The organizer’s shuttle page also lists the Signcraft Screen Printing lot, 11309 W. Chetlain Ln.
Shuttles drop off at Green Street Plaza near City Hall (101 Green St.). From there it is a short walk over the pedestrian bridge to the park. The bridge has stairs at both ends, and the fair does not provide rides from the park back to the shuttle.
Paid and accessible parking
Paid: limited spaces at the City of Galena lot, 91 Bouthillier St., near the Old Train Depot. Traffic runs one way down Bouthillier Street from Highway 20 toward the lot.
Accessible: very few spaces at the Old Train Depot lot, 101 Bouthillier St. Show your permit to the attendant at Bouthillier and Park Avenue, and you’ll be directed in if a space is open. Accessible parking is no longer available on Johnson Street.
Our tip: for groups staying in The Galena Territory, don’t try to park near the park. Drive to one of the free remote lots and take the shuttle. Plan extra time before heading downtown on Saturday, because fair traffic builds through the morning.
If someone in your group has limited mobility, plan around the bridge stairs. The accessible spaces at the Depot are the only close option and there are very few, so arriving right at opening gives you the best chance.
Restrooms: portable restrooms are at the southwest and northeast ends of the park, with accessible units near Johnson Street and by the large pavilion. Permanent public restrooms are downtown at City Hall and at Hello Galena!, 121 N. Commerce St.
06 · Where to stay
Where to stay for the Galena Country Fair
Most of our homes are in The Galena Territory, a large wooded resort community east of downtown Galena. It is not downtown, and we’d rather you know that before you book. Here is the honest tradeoff for fair weekend:
| Downtown Galena | The Galena Territory and nearby | |
|---|---|---|
| Getting to the fair | Walkable from many downtown lodgings | Drive to a remote lot, then shuttle |
| Space | Mostly rooms, suites and smaller rentals | Whole homes, most with 2 to 5 bedrooms, and full kitchens |
| Groups | Often split across several rooms | Everyone under one roof |
| Evenings | Main Street restaurants and bars on foot | Quiet and wooded; hot tubs, fire pits or fireplaces at select homes |
| Parking | Tight on fair weekend | Driveway parking at the house |
If Country Fair is the main reason for your trip and walking to Main Street matters most, stay downtown. If you’re coming with family or friends and want room to spread out after a day on your feet, a vacation home makes more sense than splitting up across several hotel rooms.
We’re a small, locally owned team, and we hold every home to the same standard: cleaned and turned over by our own crew, checked on regularly, and a text away while you’re here. Comfortable and well kept, not fussy.
What to look for in a vacation home for fair weekend
Enough bathrooms, not just beds
Everyone gets ready for the fair at the same time on Saturday morning. For groups of six or more, look at the bathroom count as closely as the bedroom count.
A kitchen you’ll actually use
Restaurants are packed fair weekend. A full kitchen and a big table mean you can do breakfast and at least one dinner at the house.
Somewhere to unwind after
October evenings get cool. Select homes have a hot tub, fire pit or fireplace, depending on the property; use the amenity filter in the search above.
Bringing your dog?
Select homes are pet-friendly, and dogs are welcome to come along for the weekend. Since the fair itself doesn’t allow pets, your dog should be house-trained, well behaved and comfortable being crated while you’re out. Check the home’s pet policy before you book.
07 · Questions
Galena Country Fair FAQs
When is the Galena Country Fair in 2027?
Saturday, October 9 and Sunday, October 10, 2027. The fair is held every year on Columbus Day weekend.
What are the Galena Country Fair hours?
The organizer has not posted 2027 hours yet. In 2026 the fair ran 10 a.m. to 5 p.m. Saturday and 10 a.m. to 4 p.m. Sunday. We’ll update this page when 2027 hours are published.
Where is the Galena Country Fair held?
Grant Park, 625 Park Avenue, Galena, Illinois. The park is on the east side of the Galena River, across the pedestrian bridge from downtown.
Is the Galena Country Fair free?
There is a suggested donation at the gate, $3 in 2026. The fair is volunteer-run and the money goes to nonprofits in Jo Daviess County.
Where do I park for the Galena Country Fair?
Use the free remote lots (Walmart, Galena High School and the Alice T. Virtue Pool) and ride the free shuttle, which ran every 30 minutes from 8 a.m. to 6 p.m. in 2026. Limited paid parking is at the city lot near the Old Train Depot, 91 Bouthillier St.
Can I bring my dog to the Country Fair?
No. Only trained service dogs are allowed in Grant Park during the fair. Emotional support animals are not permitted.
What happens if it rains?
The fair goes on rain or shine. There is no rain date and no indoor location, so bring rain gear and shoes you don’t mind getting muddy.
Where should I stay for the Galena Country Fair?
Downtown lodging is best if you want to walk to the fair and Main Street. For families and groups who want more space, a vacation home in The Galena Territory works well; drive to a free remote lot and take the shuttle in. Use the live search on this page to see homes for your dates.
Is there a minimum stay for Country Fair weekend?
Yes. Our Galena homes have a 3-night minimum over Country Fair weekend. We recommend arriving Friday, October 8 and leaving Monday, October 11, 2027 (Columbus Day).
How long do people spend at the fair?
Usually two to four hours. One morning at the fair plus a day for Main Street and the surrounding area is a comfortable pace.
More for your Galena trip
- Galena vacation rentals from The Collection
- Halloween weekend in Galena, three weeks after the fair
- Our Explore Galena guide
- Rental FAQ: check-in, policies and what’s provided
Find a home for Country Fair weekend
Friday, October 8 to Monday, October 11, 2027. Search current availability and rates, or email us with questions about which home fits your group.
Search current availability Email usSources. Event details are from the official Galena Country Fair site (schedule, event FAQs, parking and shuttle, food and drink, about), cross-checked with Visit Galena’s Country Fair Insider Guide. Lodging advice, minimum stays and home details are ours. Last verified September 29, 2026.
The Collection Vacation Homes is a locally owned vacation rental company in Galena, Illinois, and is not affiliated with the Galena Country Fair.