Lakeside Festival At the Dole
Best Summer Event
This festive four-day event, held annually around Independence Day, features such warm-weathered favorites as a parade, carnival rides, a baggo tournament, fireworks and a full menu of food and beverages. A variety of kiddie-themed attractions are also included in each year’s itinerary, including a magician, a balloon twister, a face painter, a stilt walker and team mascots. Festival guests are also free to enjoy the live music performances on multiple stages scattered across the grounds.
Location: Dole Mansion, 401 Country Club Road, Crystal Lake, IL
thedole.org | 815-455-8000
Fair Diddley
Best Spring Event
This juried arts and crafts show is traditionally held the third Sunday in May within the historic grounds of Woodstock Square. In any given year, more than 300 crafters typically showcase their handmade creations. Proceeds from the event benefit the McHenry County Mental Health Resource League.
Location: 121 W. Van Buren St., Woodstock, IL
mhrl.org/fairdiddley | 815-385-5745
Walworth County Fair
Best Summer Event
Walworth County’s annual late summer fair is one of the longest in the area, running for six days, typically from the Wednesday prior to Labor Day through Labor Day itself. The event, which has been in existence for more than 170 years, features a number of enjoyable attractions including animal barns, carnival rides, exhibits, judging contests and music performances.
Location: Walworth County Fairgrounds, 411 E. Court St., Elkhorn
walworthcountyfair.com | 262-723-3228
Huntley Fall Fest
Best Fall Event
Over the years, this late September extravaganza has offered up a heaping helping of family-friendly, autumn-themed entertainment and activities, including a 5K run, car and tractor shows, hay rides, a model train display, a pancake breakfast and scarecrow building contest. Throughout its three days, the festival also features a variety of live music performances and a carnival.
Location: Deicke Park, 12015 Mill St., Huntley, IL
huntleyfallfest.com | 847-669-8935
Winterfest
Best Winter Event
The centerpiece of this annual mid-winter extravaganza, held early each February, is the snow sculpting contest, which draws participants and visitors from throughout the country. Entrants each year concoct a variety of larger-than-life creations over the course of the competition’s three days, after which each entry remains on display until it melts. Other frosty festivities throughout the duration of Winterfest include a sculpture tour, bonfires on the beach complete with s’mores, a cocoa crawl, a fire and ice bar and hovercraft rides.
Location: Riviera Plaza and Flat Iron Park, Downtown Lake Geneva, WI
visitlakegeneva.com | 262-248-1000
Groundhog Days
Best Winter Event
Since the release of “Groundhog Day,” Bill Murray’s 1992 comedic hit movie, set in Woodstock, town organizers have celebrated the film’s influence on the community. Each year on February 2, the town comes alive with activities, including a chili cook off, breakfast, dances and special screenings of the flick in addition to a tour of the filming sites — including the very locale of Woodstock Willie’s proclamation. Since its inception, visitors from across the globe have flocked to Woodstock to celebrate Groundhog Day.
Location: Throughout Woodstock, IL
woodstockgroundhog.org | 815-334-2620
Venetian Festival
Best Local Festival
This annual five-day festival, hosted by the Lake Geneva Jaycees every August, is filled with family entertainment. Founded in 1962, the festival includes a craft fair, a carnival and a water ski show, after which the festival is capped off with a traditional Venetian-style lighted boat parade, paired with the area’s largest firework display over Geneva Lake. The event takes place across downtown Lake Geneva, including Flat Iron, Library and Seminary Parks, and attracts tens of thousands of visitors from across the country.
Location: Throughout Downtown Lake Geneva, WI
venetianfest.com | 815-334-2620
Music by the Lake
Best Outdoor Live Music
While George Williams College of Aurora University is an educational institution, it is also known by music fans as host to its celebrated summer performance series, Music by the Lake. Back in 1951, a group of full- and part-time residents banded together, forming the George Williams College Summer Music Association, and their first order of business was producing a summer concert series. After 19 seasons, rising costs had silenced the musical program, but in 2001, Music by the Lake once again became a tradition of community. The hilly, 130-acre shoreline campus provides a cherished experience for its guests. Trying to make it more personal, Aurora University aims to not exceed 2,000 attendees, so that it feels more intimate. The staff and volunteers help guests unload their picnic belongings onto the lawn as well as shuttle guests in golf carts across the property. Those attending are advised to park in a nearby lot at Williams Bay High School and board a shuttle downhill to the venue. Those with lawn seats can bring their own basket, or visit one of several food stations selling popcorn, hot dogs and burgers, or pop in the College Inn for a sandwich, salad or ice cream. Beer, wine and Champagne are available for purchase for those seated in the pavilion and terrace.
Location: 350 Constance Blvd, Williams Bay, WI
musicbythelake.com | 262-245-8501
