Annual Lighting of the Square, held on the Friday after Thanksgiving, this celebration kicks the Holiday season downtown. After dark, crowds gather in the Square, sing carols and mingle around the local shops. At 7:00 p.m., a small presentation is made by the mayor, City council representative and even Santa Claus. After Miss Woodstock speaks, the crowd counts down in unison and she throws the big light switch. All at once, Christmas lights in all the park trees and atop every building's facade turn on in a dazzling and festive introduction to the season.
Groundhog Day, the town celebrates "Groundhog Day" at the beginning of every February, including tours of famous filming sites from the 1993 movie. The town now even has its own groundhog named "Woodstock Willie", who essentially performs the same tasks as "Punxsutawney Phil" at the site of the original Groundhog Day festival. Every year on the weekend of Groundhog Day, the Classic Cinemas Woodstock Theater shows Groundhog Day for free. Woodstock's Groundhog day festival also includes a traditional groundhog lighting.
The historic Woodstock Square, the square consists of historic buildings and is anchored by two key structures, the Old McHenry County Courthouse and the Woodstock Opera House. Most of the other buildings on the square are privately owned and kept up, housing numerous small businesses, including restaurants and shops. The streets of the square are one way and paved with brick, they square off a large public park which features two gazebos and war memorials. During the winter the square and its buildings and trees are adorned with lights.
The Woodstock Opera House has been in continuous operation since its construction was completed in 1889. Along with the Old Courthouse, the Opera House is one of the key elements of the Woodstock Square Historic District. Originally constructed to be a library, council room, court, fire department, and provide a second floor auditorium, the Opera House quickly became the center for McHenry County's entertainment. Today the Opera House hosts a variety of events. They include: concerts, theatre, dance, visual art, educational programs, lectures and meetings. The Woodstock Opera House is one of the oldest continually operating theatres in the United States.
The Illinois Railway Museum, Illinois Railway Museum is the largest railroad museum in the United States and is located in nearby Union, Illinois
For more events and attractions click here to visit the Woodstock Chamber of Commerce.
Three Brothers Family Restaurant, adjacent to the Best Western Woodstock Inn. Three Brothers Family Resuaruant offers American and Greek fare for breakfast, lunch and dinner and offers full bar. Phone (815) 338-5606
Napoli Pizza, also adjacent to the Best Western Woodstock Inn, "Famous For Pizza", Family Owned and Operated Pizzaria offers Dine-In, Pick-Up or Delivery. Phone (815) 338-2430
Vaughan's Family Restaurant, less than 1 mile from the Woodstock Best Western Inn, offers hearty American fare with daily specials and an All You Can Eat Fish Fry on Fridays. Phone (815) 338-3391
- Crystal Lake, 10 Miles
- Mchenry, 15 Miles
- Algonquin, 21 Miles
- Elgin, 25 Miles
- Rockford 30 Miles
- Lake Geneva Wisconsin, 35 Miles
- Chicago, 50 Miles
- O'Hare International Airport, 45 Miles
- Midway Airport, 65 Miles
- Milwaukee Airport, 80 Miles
- Metra Train Station, 1 Mile