ST. PATRICKS DAY – March 17th  Join in the fun this St. Patrick’s Day with a 5k Shamrock Shimmy Race downtown, starts at 8am. And don’t forget the St. Patrick’s Day Parade at 4pm on Main St. More information on these events can be found on the Visit Galena website.

WINE LOVER’S WEEKEND – March 23rd-24th Sip your way though one of Illinois largest indoor wine tastings with over 250 wines to choose from! This is a two-day event of great wine, food, and friends. And take part in Wine Pairing Luncheon at the Galena Cellars Vineyard from 12-3pm on Saturday. And the Beer Pairing Dinner at the Galena Brewing Company on Main St, Saturday the 23rd from 6pm-8pm. Click here for more information.


SPALESS WEEKEND – APRIL 6th-7th Join the sisterhood of Spaless Weekenders and show off your crazy hats and colorful tutu’s! Enjoy a weekend of eating, drinking, shopping, dancing, and visiting. For more information visit

GRANT’S BIRTHDAY WEEKEND – APRIL 20th-22nd Celebrate the birthday of our 18th president here in Galena. Activities include, battle reenactments, performances by the Women of Courage and Commitment, a pie auction, and of course tour Grant’s home and the Grant Museum.

GRANT’S HOMEFRONT REENACTMENT – APRIL 27th-28th Located in Depot Park, this two event showcases how they lived during the civil war with battle reenactments, a sanitary fair, bazaar, and tours of Grant’s home.


MAIN STREET SIDEWALK SALE – May 12th-14th Calling all shoppers!! This is a great weekend to get to Galena and join the Main Street merchants for their spring cleaning shopping event. Sales will be on the sidewalks as well as in stores, do not miss this opportunity for spring savings!

GALENA RIVER TRAIL RUN – MAY 19th Bring your running shoes and join the race on the Galena River Trail. Races include a 10k (runners only), 5k (run or walk), and also a kids fun run.

GALENA SKY TRAIL RACE – MAY 19th Do you like to run? This course is set on the trails of Chestnut Mountain Resort, the same hills used to ski on in the winter. Enjoy the majestic views of the Mississippi River where you can see Iowa and Wisconsin across the river! More details can be found on Chestnut Mountain’s website.


CEMETERY WALK – JUNE 9th-10th Presented by the Galena-Jo Daviess County Historical Society, the 25th Cemetery walk will be held at Greenwood Cemetery Sat. and Sunday. Watch as local performers portray individuals buried in Galena’s Greenwood Cemetery and recount their lives.

GREAT GALENA BALLOON RACE – JUNE 15th-17th A spectacular three-day event with more than 20 hot air balloons, three races, an evening glow extravaganza, car show, and more! Also a wine flight on Saturday! Details can be found on Eagle Ridge’s website.

CORKLESS IN GALENA – JUNE 23rd Sample select wines produced by family owned Northern Illinois Wineries. Spend the day enjoying food, art, and live music!


INDEPENDENCE DAY CELEBRATION – JULY 4th Celebrate our countries birthday with activities all around the town, annual 4th of July parade, and fireworks at dusk.


LADIES GETAWAY WEEKEND – SEPTEMBER 7th-9th Grab your girls and head to Galena for a weekend of shopping, partying, laughing, and more!

12th ANNUAL GALENA OKTOBERFEST – SEPTEMBER 22nd Get to Galena for our 12th annual Oktoberfest celebration is Depot Park. Enjoy live music, german style food and beverages, wiener dog races, and more.

51ST ANNUAL TOUR OF HISTORIC HOMES – SEPTEMBER 29th-30th Take a guided tour of 5 of Galena’s historic beautiful homes.


COUNTRY FAIR WEEKEND – OCTOBER 6th-7th Visit Galena for one of their most popular events. A weekend of over 150 vendors selling a variety of hand crafted original works of art, crafts, and fine arts. Also find family fun, entertainment, food, raffles, and more.