A $55 ticket to this year's candlelit holiday concert at St. Mark's Episcopal Church comes with a $20 dining voucher. You can spend it at any of 25 downtown Glen Ellyn restaurants through Jan. 31, 2027. Most of the 2026 holiday calendar works the same way. Ladies Night Out starts at a store you choose. The tree lighting rolls straight into an hour of downtown shopping. The Ugly Sweater Dine Around starts at a restaurant you pick when you buy your ticket. Taken together, the season is a series of ways to steer an evening through Main Street, Crescent Boulevard and Pennsylvania Avenue. If you know how each event works, you can plan the night around it.
Here's the calendar in order, with the details that affect your plans.
Nov. 5 and 12: Ladies Night Out, and why the store you pick matters
Ladies Night Out is back for its 19th year. It runs on two Thursday evenings, Nov. 5 and Nov. 12, so it's less crowded than it would be on one night. The Alliance of Downtown Glen Ellyn sells tickets through its Ladies Night Out ticket page, and the rules decide how your evening goes:
- Tickets cost $22 and cover five 3-ounce wine pours, nonalcoholic drinks, small bites, and discounts at the shops.
- The event runs 5 to 9 p.m. and is 21 and over.
- When you buy, you choose the store where you'll pick up your wristband and program. That's only your first stop. After that you can visit any of the 20+ participating shops.
- Drinks stay inside the stores, one per store, and can't go out on the sidewalk.
- Tickets are non-refundable, and none are sold that night.
Pick a shop at the far end of your route and you walk past everything else with fresh discounts in hand. The evening is also meant to end at a restaurant. The ticket page says downtown restaurants will serve special menus and cocktails for Ladies Night Out and that a full list is coming.
Thanksgiving week: one free morning, then the holiday kickoff
Thursday, Nov. 26: the Turkey Trot
The Glen Ellyn Park District's Turkey Trot 4-Mile Run is the one big event this season with no ticket and no restaurant tie-in. It's free and runs 8 to 10 a.m. at Lake Ellyn Park. You don't need to register, but you do have to sign a waiver beforehand to be eligible.
It's also a "Predicto Race." According to the Park District's winter program guide, the two runners whose predicted finish times come closest win a Thanksgiving treat. Timing devices aren't allowed on the course, so leave the GPS watch at home. Speed doesn't win you anything, though there's a prize for best costume. The Park District collects non-perishable food at the race for the Glen House Food Pantry.
Friday, Nov. 27: the Library first, then the tree
The Glen Ellyn Public Library holds its own Holiday Walk the same evening, with music and light refreshments before the downtown walk. It's an easy place for a family to start the night.
The Downtown Alliance calendar lists the Holiday Walk & Tree Lighting schedule:
- 5 p.m. The street opens.
- 6 p.m. Santa lights the tree.
- 6:30 to 7:30 p.m. Downtown shopping, Santa photos, and hot cocoa at the fire station.
The event is free. Like Ladies Night Out, it ends in the stores, which get a full hour once the tree is lit.
Nov. 27 is also the start date for several things that run the rest of the season:
- Santa's Mailbox returns to the northeast corner of Main Street and Crescent Boulevard. Letters "mailed" by Sunday, Dec. 13 get a reply from Santa and a signed photo, so include a legible return address.
- The Snow Globe Stroll, a holiday-window scavenger hunt, runs downtown through Dec. 31.
- Project Light Up Glen Ellyn brings extended shop hours, seasonal restaurant menus, and lit-up streets. The Village lists it from Nov. 27 through Dec. 31. The Alliance describes it as running from mid-November through the New Year.
Weekends from Nov. 28: Santa House
From Nov. 28 through Dec. 20, Santa visits the Santa House at 425 Main St. on weekends, with strolling carolers. The Alliance lists hours as Saturdays and Sundays, 10:30 a.m. to 12:30 p.m., and notes that times may vary. Visits are free, and pets are welcome in the photos.
The Glen Ellyn Chamber of Commerce is also hosting free family movies at the Glen Art Theatre throughout November and December. The Village lists them on Saturdays. Check the Chamber page for titles before you go. A movie on a Saturday afternoon pairs easily with a Santa House visit that morning.
Saturday, Dec. 5: the concert that pays for part of dinner
The Downtown Glen Ellyn Illuminated Concert Series presents "Holiday Magic" at St. Mark's Episcopal Church, 393 Main St. Midtown Strings will play holiday and winter favorites surrounded by more than 1,000 LED candles. The program includes selections from The Nutcracker, "Christmastime Is Here," and "Somewhere in My Memory" from Home Alone.
There are three shows, each about an hour long and each with its own reception beforehand:
| Reception | Performance | Notes |
|---|---|---|
| 2:30 p.m. | 3:30 to 4:30 p.m. | Family matinee, free Santa photos |
| 5:00 p.m. | 5:45 to 6:45 p.m. | |
| 7:15 p.m. | 8:00 to 9:00 p.m. |
Cabernet & Company hosts the reception. Your $55 ticket includes one drink there, such as wine, beer, hot cocoa or hot cider, and extra drinks are $10. You get the $20 voucher when you arrive. You can combine several vouchers on one check, but unused balances don't give cash back.
You don't have to spend the voucher that night, and that changes how you plan. It's good through Jan. 31, 2027, so a 5:45 show and a January dinner can be planned separately. The 25 restaurants on the concert page include a toda madre, Barone's of Glen Ellyn, Blackberry Market, Common Good Cocktail House, Curry à la Flambé, fire+wine, ko-ze wine room, Maize + Mash, Maplewood Public House, Marinella Italian Restaurant, MK Steak + Bar, Shannon's Irish Pub, Sushi Ukai, The Beer Cellar, The Parlour of Park & Oak, Pete's Ice Cream and Chocolaterie Stam.
Mancini's Tavola is on the list too, and this is its first holiday season downtown. Patch reported that A Tavola by Mancini opened Feb. 10, 2026, at 504 Crescent Blvd.
A few practical points from the Alliance:
- Seating is general admission, first come, first served. The performance starts on time, so plan to arrive at least 15 minutes early.
- The church is fully ADA accessible.
- Ticket sales are final. If you can't make it, the Alliance says your voucher may be mailed to you.
- The Alliance suggests parking in the Village Parking Garage.
The page still lists tickets as "coming soon."
Wednesday, Dec. 9: the Ugly Sweater Dine Around
The Ugly Sweater Dine Around works like Ladies Night Out, with restaurants in place of boutiques. You choose a restaurant to check in at first and then make your way around the other participating spots. Tickets go on sale Nov. 1. Last year's Dine Around page is still online with older prices, so go by the current events calendar for this year's details.
You can join the season's other contest from your own front yard. The Glen Ellyn Home Holiday Lights Contest is open for registration and runs through December. Categories are Most Festive, Best Use of Lights, Most Creative, and The Clark Griswold Award.
The corner with the Santa mailbox is next in line for change
Santa's Mailbox stands at Main and Crescent, the edge of the block the Village plans to rebuild. According to the Village's Sept. 16 train station update, the new Metra station and pedestrian underpass include the fourth phase of the downtown streetscape project. Crescent Boulevard between Main and Park, and Forest Avenue between Duane and Pennsylvania, will get new underground utilities and then rebuilt streets and sidewalks. The plan also calls for a new station building, warming shelters, more bicycle parking, and an ADA-accessible underpass beneath the tracks.
Patch reported that the Village Board was scheduled to vote Oct. 26 on a special-use permit and zoning variations for the project at 545–581 Crescent Blvd., after the Plan Commission recommended approval in September. The Village has said these reviews cover design and zoning, not a construction contract. If easement talks with Union Pacific go well, bidding could happen in summer 2027 and construction could start as early as fall 2027. On that timeline, no station construction overlaps this year's holiday calendar.
For the full list of dates in one place, the Village keeps a Fall & Winter Special Events notice with links to each organizer.
At DPG Real Estate Agency, we're glad to see downtown Glen Ellyn put this much into its holiday season, and we keep up with the changes on Crescent Boulevard as they come. If you have questions about the neighborhood or what's next for downtown, we're happy to talk it through.
