Plan your holiday schedule in Bridgeport with ease! Our guide has all the top festive events. Whether you're deeply connected to Bridgeport or just making connections, this guide illuminates the seasonal offerings.
This season, Winter WonderFest at Navy Pier captures the festive spirit with its dazzling decorations and fun-filled activities for families. Plus, the enchanting Lightscape at Chicago Botanic Garden transforms the gardens into a winter wonderland, featuring stunning light displays and joyful installations. And the Galena Cellars Nouveau Weekend offers a delightful taste of locally produced wines to celebrate the season. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Bridgeport
- Winter WonderFest at Navy Pier (Chicago)
- Wonderland Express & Lightscape at Chicago Botanic Garden (Glencoe)
- Galena Cellars Nouveau Weekend (Galena)
- Evanston Winter Craft Fair (Evanston)
- Lunch with Santa on the Train (Monticello)
- Winter Wonderland Drive-Thru Light Show (Wallingford)
- Bridgeport Christmas Tree Lighting
- Holiday Showcase + GLOW (Monticello)
- Caroling at the Carillon (Springfield)
- Christmas Village (Torrington)
See these and even more events listed below!
Bridgeport Holiday Light Displays
Wonderland Express & Lightscape at Chicago Botanic Garden
What to Expect:
Seasonal light displays and decorations in a botanical garden setting.
Description:
Explore the Chicago Botanic Garden's Wonderland Express & Lightscape, featuring intricate light displays and seasonal decorations that transform the garden into a vibrant winter wonderland.
Where: Glencoe | More Info: Wonderland Express & Lightscape at Chicago Botanic Garden
Winter WonderFest at Navy Pier
What to Expect:
Dazzling outdoor light displays and ice-skating rink.
Description:
Light Up the Lake at Navy Pier features dazzling outdoor lakefront light displays, an outdoor ice-skating rink, cozy firepits, and the heated Centennial Ferris Wheel. Skating is free if you bring your own skates.
Where: Chicago | More Info: Winter WonderFest at Navy Pier
Bridgeport Christmas Tree Lighting
What to Expect:
Community-wide countdown and historical tree lighting tradition.
Description:
The Bridgeport Christmas Tree Lighting transforms the city center into a vibrant holiday scene with a community-wide countdown and the illumination of a massive evergreen tree, dating back to 1931. Local choirs perform seasonal favorites, and the air is filled with the aroma of hot cocoa.
Where: Bridgeport | More Info: Bridgeport Christmas Tree Lighting
Winter Wonderland Drive-Thru Light Show
What to Expect:
Dazzling holiday light displays with iconic characters.
Description:
A dazzling drive-through holiday lights experience featuring over a mile of spectacular light displays, including a larger-than-life sparkling Holiday Barbie display, a supersized Bigfoot Monster Truck, and life-sized dinosaurs in Prehistoric Christmas.
Where: Wallingford | More Info: Winter Wonderland Drive-Thru Light Show
Bridgeport Holiday Markets and Shopping
Evanston Winter Craft Fair
What to Expect:
Month-long event featuring diverse handmade crafts.
Description:
The Evanston Winter Craft Fair showcases over 140 selected artisans featuring original, handmade works of jewelry, ceramics, fiber, metal, glass, painting, photography, and mixed media.
Where: Evanston | More Info: Evanston Winter Craft Fair
Bridgeport Holiday Shows and Entertainment
Caroling at the Carillon
What to Expect:
Family-friendly holiday celebration with caroling and festive activities.
Description:
Gather around a roaring bonfire to sing Christmas carols accompanied by the beautiful music of the Thomas Rees Memorial Carillon. Enjoy family-friendly activities, including crafts, photo ops, and visits with Santa, along with complimentary snacks and drinks.
Where: Springfield | More Info: Caroling at the Carillon
Holiday Showcase + GLOW
What to Expect:
Elegant holiday celebration with artisan markets and festive performances.
Description:
The Holiday Showcase + GLOW event at Allerton Park & Retreat Center features specially-selected artisans, a lunch buffet, carriage rides, and festive performances in the Mansion and Formal Gardens.
Where: Monticello | More Info: Holiday Showcase + GLOW
Holiday Affair
What to Expect:
Elegant holiday ball with champagne, hors d'oeuvres, and live music.
Description:
Join us for an elegant evening at the Holiday Affair presented by Ion, featuring a welcome glass of champagne, hors d'oeuvres, and a cash bar. Enjoy dinner served by Chef DeAngelo Newson at 6 p.m., including complimentary wine, followed by post-dinner music and dancing. Black tie optional.
Where: Monticello | More Info: Holiday Affair
Winter Solstice Bonfire
What to Expect:
Traditional bonfire celebration with local food and shopping.
Description:
Celebrate the winter solstice with a bonfire in the Allerton Meadow, strolling through Holiday GLOW, and shopping at The Farms Winter Market in the Mansion. Enjoy meals from food trucks and beverages from the bar.
Where: Monticello | More Info: Winter Solstice Bonfire
Bridgeport Other Holiday Activities
Galena Cellars Nouveau Weekend
What to Expect:
Traditional horse-drawn wagon parade delivering Nouveau wine to local merchants.
Description:
Galena Cellars Nouveau Weekend is a celebration of the annual release of Le Beaujolais Nouveau, featuring a parade of revelers, live music, wine tastings, and dinner specials. Local restaurants and businesses join in the festivities with traditional French fare and merriment.
Where: Galena | More Info: Galena Cellars Nouveau Weekend
Lunch with Santa on the Train
What to Expect:
Unique dining car experience with Santa visit.
Description:
Join us for Lunch with Santa on the Train at the Wabash Depot in Monticello, Illinois. Enjoy a train ride, individual visit with Santa, and a kid-friendly sack lunch. This event offers both coach tickets and a Deluxe Dining Car experience with turkey sandwiches, chips, cookies, and commemorative keepsakes.
Where: Monticello | More Info: Lunch with Santa on the Train
Holiday Cookie Decorating
What to Expect:
Hands-on cookie decorating with expert guidance.
Description:
Decorate holiday cookies in a festive setting with guidance from experienced instructors, perfecting your holiday baking skills.
Where: Monticello | More Info: Holiday Cookie Decorating
Holiday Wreath Making
What to Expect:
Guided class using natural and specialty materials.
Description:
Create a beautiful holiday wreath using natural greens, pods, and specialty materials harvested from Monticello's gardens. Led by expert floral designers and gardeners, participants will learn the art of crafting a seasonal decoration that will adorn their door throughout the season.
Where: Monticello | More Info: Holiday Wreath Making
Holiday Mansion Tours
What to Expect:
Intimate look at holiday celebrations on Monticello's mountaintop.
Description:
Explore Monticello after dark, decorated with holiday greenery from Jefferson's era. Journey through public and private rooms, including the iconic Dome Room, to see how enslaved and free people celebrated holidays.
Where: Monticello | More Info: Holiday Mansion Tours
Sensory Hour Sweets with Santa
What to Expect:
Sensory-friendly holiday event with Santa, crafts, and treats.
Description:
Children can chat and get their picture with Santa, hear a story from Mrs. Claus, create crafts, and enjoy festive treats in a quieter environment at Allerton Mansion.
Where: Monticello | More Info: Sensory Hour Sweets with Santa
Sweets With Santa
What to Expect:
Interactive holiday activities with Santa and Mrs. Claus.
Description:
Join Santa Claus at the Allerton Park & Retreat Center for a delightful afternoon of holiday activities. Children can chat with Santa, read a story with Mrs. Claus, create their own crafts, and enjoy festive treats.
Where: Monticello | More Info: Sweets With Santa
Christmas Village
What to Expect:
Interactive holiday experience with Santa, Mrs. Claus, and elves.
Description:
Visit Christmas Village in Torrington, CT, where children and adults can meet Santa, Mrs. Claus, and four reindeer, and see the elves hard at work. Each child receives a small gift from Santa, and there is a hot cocoa booth to warm up while waiting. This year, multiple food trucks will be available.
Where: Torrington | More Info: Christmas Village
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Chicago (1 miles)
- Lower West Side (1 miles)
- Douglas (2 miles)
- Near South Side (2 miles)
- New City (2 miles)
- Grand Boulevard (2 miles)
- Brighton Park (3 miles)
- South Lawndale (3 miles)
- Chicago Loop (3 miles)
- Gage Park (4 miles)
- North Lawndale (4 miles)
- East Garfield Park (4 miles)
- Englewood (4 miles)
- West Town (4 miles)
- West Englewood (4 miles)
- Hyde Park (4 miles)
- Near North Side (4 miles)
- Woodlawn (5 miles)
- Chicago Lawn (5 miles)
- Cicero (5 miles)
- Greater Grand Crossing (6 miles)
- Lincoln Park (6 miles)
- West Lawn (6 miles)
- Logan Square (6 miles)
- South Shore (6 miles)
- Auburn Gresham (7 miles)
- Ashburn (7 miles)
- Chatham (7 miles)
- Berwyn (7 miles)
- Oak Park (8 miles)
- Avondale (8 miles)
- North Center (8 miles)
- South Chicago (8 miles)
- Uptown (9 miles)
- Belmont Cragin (9 miles)
- Irving Park (9 miles)
- Lincoln Square (10 miles)
- Albany Park (10 miles)
- Burbank (10 miles)
- Edgewater (10 miles)
- Portage Park (10 miles)
- Morgan Park (10 miles)
- Maywood (10 miles)
- Oak Lawn (10 miles)
- West Ridge (11 miles)
- Melrose Park (11 miles)
- Rogers Park (12 miles)
- Blue Island (13 miles)
- Dolton (14 miles)
- Skokie (14 miles)
- Niles (15 miles)
- Park Ridge (15 miles)
- Elmhurst (15 miles)
- Morton Grove (16 miles)
- Harvey (16 miles)
- South Holland (17 miles)
- Wilmette (17 miles)
- Calumet City (17 miles)
- Oak Forest (17 miles)
- Westmont (17 miles)
- East Chicago (17 miles)
- Glenview (17 miles)
- Darien (18 miles)
- Villa Park (18 miles)
- Orland Park (18 miles)
- Des Plaines (18 miles)
- Addison (19 miles)
- Lombard (19 miles)
- Downers Grove (19 miles)
- Tinley Park (20 miles)
- Lansing (20 miles)
- Elk Grove Village (20 miles)
- Munster (20 miles)
- Woodridge (22 miles)
- Mount Prospect (22 miles)
- Glen Ellyn (22 miles)
- Glendale Heights (22 miles)
- Lisle (22 miles)
- Northbrook (22 miles)
- Homer Glen (22 miles)
- Highland (22 miles)
- Chicago Heights (23 miles)
- Gary (23 miles)
- Wheaton (24 miles)
- Bolingbrook (24 miles)
- Bloomingdale (24 miles)
- Park Forest (24 miles)
- Roselle (24 miles)
- Highland Park (25 miles)
- Rolling Meadows (25 miles)
- Wheeling (25 miles)
- Carol Stream (25 miles)
- Naperville (26 miles)
- Romeoville (26 miles)
- Hoffman Estates (26 miles)
- Schererville (27 miles)
- Buffalo Grove (27 miles)
- Lockport (27 miles)
- Palatine (27 miles)
- Hanover Park (28 miles)
- New Lenox (28 miles)
- West Chicago (29 miles)
- Hobart (29 miles)
- Merrillville (30 miles)
- Bartlett (30 miles)
- Streamwood (30 miles)
- Crest Hill (30 miles)
- Portage (30 miles)
- Joliet (31 miles)
- Vernon Hills (31 miles)
- Plainfield (32 miles)
- Crown Point (33 miles)
- Geneva (34 miles)
- Batavia (34 miles)
- St. Charles (34 miles)
- Libertyville (34 miles)
- Mundelein (34 miles)
- South Elgin (35 miles)
- Aurora (35 miles)
- North Chicago (35 miles)
- Elgin (35 miles)
- Carpentersville (37 miles)
- Oswego (38 miles)
- Gurnee (39 miles)
- Wasco (39 miles)
- Valparaiso (40 miles)
- Michigan City (40 miles)
- Algonquin (40 miles)
- Grayslake (40 miles)
- Lake in the Hills (42 miles)
- Zion (43 miles)
- Round Lake Beach (43 miles)
- Crystal Lake (44 miles)