Ugly Sweater Food Tour: Galena Main Street, 5 stops

An ugly sweater contest runs alongside the tastings, with a free tour as the prize.

The Ugly Sweater Food Tour is a holiday-themed food walk down Main Street in Galena, Illinois, where you stop at five local restaurants and specialty shops to sample regional dishes, craft beverages and seasonal drinks. The tour runs about two and a half hours and includes all food tastings, water, a custom lanyard and a holiday gift. Up to three alcoholic tastings are part of the experience for guests 21 and older. Wear an ugly Christmas sweater to enter the contest for a free tour. The 10:30am departure includes one step and incline, while the 1pm tour has a flight of stairs. Late arrivals can usually join by the first stop.

Step-by-step itinerary

Festive food tour in Downtown Galena

• Stroll through Downtown Galena
• Sample flaky and soft empanada
• Try secret menu item and bonus tastings
• Enjoy holiday shopping and spirits tasting
• Explore root beer soda and specialty sodas
• Experience Mediterranean tapas and sangria
• Enjoy craft tap beer with coastal delights and dessert

The experience

Dig out that ugly Christmas sweater. You'll wear it through a stroll down Main Street as your festive foodie guide leads you through five stops that showcase how Galena celebrates the holidays. The tour wraps the town's best food and drinks in a seasonal theme, so you're not just tasting. You're seeing how the Hallmark of the Midwest transforms in December. All food tastings are included in the ticket price, so you arrive with an empty stomach and leave having sampled everything from a flaky empenada at a local bakery to Spanish tapas and sangria at one of the taphouses.

The stops move through a range of flavors and formats. You'll learn the story behind the bakery owners while tasting their signature empanada, then move into secret menu items and bonus tastings at another location. A specialty soda shop introduces you to the rise of craft sodas across the country, and depending on which departure you choose, you'll either visit a Mediterranean restaurant or The Galena Taphouse for tapas. The final stop pairs locally crafted tap beer with coastal delights and dessert. Water is provided throughout, and the custom lanyard and holiday gift round out what you take home.

Guests 21 and older can enjoy up to three alcoholic tastings as part of the experience. If someone in your party doesn't drink alcohol, let the operator know beforehand so they can adjust your tastings. Vegetarians should also notify the tour in advance, as the menus are preset and coordinated with restaurant partners. The tour is wheelchair accessible, and all surfaces are accessible, though the 10:30am departure includes one step and incline while the 1pm tour has a flight of stairs. If you arrive late, you can usually join by the first stop. After that point, the tour cannot be refunded.

What’s included

• All five food tastings and drinks at each stop.
• water throughout the tour.
• up to three alcoholic tastings for guests 21 and older.
• a custom lanyard.
• a holiday gift from Galena Foodie Adventures.
• gratuities for restaurant staff.

Before you book

Days and timesSaturday and SundayDeparts at 13:00

Book up to2d before

AgesAdult (18 and older) · Child (5 to 17 years) · Under 5: can't be booked

GroupUp to 10

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsNo refund if you cancel.

Prices and times updated 8 days ago

Good to know

Low physical effortWheelchair accessibleAccessible transportStroller-friendlyPets welcomePublic transport nearby

Operated by Galena Foodie Adventures

Is this one for you?The tour starts and ends on Main Street in downtown Galena, so you don't need a car to reach the stops or navigate between them. If you're staying nearby or arrived without transportation, the walking route keeps everything contained in one festive afternoon.

Top questions

Can children come?

Yes. Ticket types: Child (5 to 17 years). Children under 5 can't be included in the booking.

What exactly do I taste at each of the five stops on the Ugly Sweater Food Tour?

You'll sample an empenada at the bakery, a secret menu item and bonus tastings at another location, specialty soda at a soda shop, Spanish tapas and sangria (or visit The Galena Taphouse depending on your departure time), and craft beer with coastal delights and dessert at the final stop. All tastings are included.

Do I have to drink alcohol on this tour, and what if I don't want to?

Up to three alcoholic tastings are part of the experience for guests 21 and older, but you can request alcohol-free tastings if you let the operator know before the tour starts. They'll adjust your menu to accommodate that request.

What's the difference between the 10:30am and 1pm departures?

The 10:30am tour includes one step and incline, while the 1pm tour has a flight of stairs. The 1pm tour visits a Mediterranean restaurant for tapas and sangria, whereas the 10:30am tour goes to The Galena Taphouse instead.

Can I join the tour if I arrive a few minutes late?

If you can join by the first stop, you can usually still participate. After the first stop, late arrivals forfeit the tour without a refund, so arriving on time is important.

Is the tour wheelchair accessible?

Yes, the tour is fully wheelchair accessible with all areas and surfaces accessible. However, the 10:30am departure includes one step and incline, while the 1pm tour has a flight of stairs, so choose the time that works best for your mobility needs.

What should I wear, and is the ugly sweater contest real?

Wear an ugly Christmas sweater to enter the contest. The prize is a free tour. It's a real contest, so dig out your most festive (or intentionally tacky) holiday sweater and you're in the running.