SEPTEMBER
Chicago Jazz Festival | Sept. 3–6, Chicago, IL
This Labor Day tradition promotes all forms of jazz in a free, three-day showcase. Presented by the Millennium Park Foundation with support from the Lloyd A. Fry Foundation, the festival blends Chicago’s local talent with national and international artists, aiming to raise awareness and foster appreciation for the long-beloved art form. chicago.gov
Irish Festival | Sept. 11–13, Pittsburgh, PA
Launched in 1991, this three-day festival is known for bringing together 25,000 people of all ages each year. The festival features a lineup of talented Irish dancers, live music and an authentic taste of Ireland from craft-made cocktails to custard. This year’s festival brings new activities and itineraries with a Celtic Wellness event and more. pghirishfest.org
The Big Four Arts Festival | Sept. 12–13, Louisville, KY
Celebrate the Big Four Arts Festival’s 10th anniversary at Louisville’s Waterfront Park. Nearly 200 juried artists showcase paintings, jewelry, ceramics and more alongside live music, food trucks and interactive art activities. Set beside the Ohio River and Big Four Bridge, the festival blends creativity, entertainment and scenic riverfront views. bigfourbridgeartsfestival.com
Woodly’s Great Gravel Adventure | Sept. 19, Elkins, WV
The West Virginia Gravel Series features six gravel cycling events across the state’s back roads and mountain terrain. Riders of all levels can choose different distances while exploring scenic climbs and rugged routes from Shinnston to Terra Alta. With a strong cycling community and challenging courses, the series highlights West Virginia’s natural beauty and adventure-riding culture. wvgravelseries.com
Detroit Black Film Festival | Sept. 23–27, Detroit, MI
This five-day annual celebration of Black filmmakers and actors is in its seventh year. Kicking off with a red-carpet, opening-night reception and concluding with an awards and honors ceremony, the festival offers screenings and other related programming, including workshops and discussions. filmfreeway.com
Ithaca Apple Festival | Sept. 25–27, Ithaca, NY
Ithaca’s annual apple festival celebrates its 44th anniversary in 2026, featuring a variety of vendors and farmers selling goods that range from ciders and pies to handmade crafts. This year also features live entertainment and community activities. The festival celebrates the businesses and community partners that make Ithaca a year-round destination. downtownithaca.com
Kitchener Waterloo Oktoberfest 2026 | Sept. 25–Oct. 17, Kitchener and Waterloo, ON
Kitchener-Waterloo Oktoberfest is Canada’s largest Bavarian-style festival, celebrating German heritage with music, food, beer halls and family events. Held from late September through mid-October, it includes signature attractions like the Thanksgiving Day Parade, KIDtoberfest and Willkommen Platz. The festival transforms the region into a lively cultural celebration for all ages. oktoberfest.ca
OCTOBER
Lotus World Music & Arts Festival | Oct. 1–4, Bloomington, IN
For 32 years, the Lotus World Music & Arts Festival has made a name for itself as a showcase for international talent. The four-day celebration hosts both musical performances and visual art showcases from local and international artists alongside vendors and includes an illuminated nighttime parade. lotusfest.org
Annual Galena Oktoberfest | Oct. 3, Galena, IL
Located in historic Galena, this German-focused fall tradition is in its 19th year. The festival boasts classic Oktoberfest offerings with a stein-hoisting contest and an abundance of bratwurst, beer and lederhosen. Don’t miss the tradition of the famous Galena Wiener Dog Races, held throughout the day. galenalions.org
Blink Cincinnati | Oct. 8–11, Cincinnati, OH
Returning to Cincinnati every two years, Blink is the nation’s largest public art festival. The event features hundreds of art installations, interactive displays and a drone show. The four-day festival features over 80 large-scale projections on some of the city’s most iconic architecture. The event’s goal is to foster a sense of community and connection through public art. blinkcincinnati.com
Parke County Covered Bridge Festival | Oct. 9–18, Multiple Locations, IN
Since 1957, this 10-day celebration spanning 10 different festival communities showcases Parke County’s 31 covered bridges. Take in the fall foliage as your backdrop while you walk one of the 10 festival locations in Parke County. Enjoy food and arts vendors at each location and check out their unique specialties. coveredbridges.com
The Ninth Annual Nostalgia Fall Classic | Oct. 16–18, Bowling Green, KY
Experience a full weekend of nostalgic racing at Beech Bend Raceway Park in Bowling Green, Kentucky, during the Nostalgia Fall Classic. The event features classic drag racing, a car show and swap meet, all set against a backdrop of vintage hot rods and high-speed competition. Fans can enjoy multiple days of racing action, with qualifying, eliminations and plenty of old-school motorsports fun. beechbend.com
NOVEMBER
Traverse City Beer Week | Nov. 6–14, Traverse City, MI
Get ready for this annual fall celebration of northern Michigan’s craft brewery scene. The week-long event features special releases from Traverse City favorites, prizes to win, group tours to join and a beer passport to fill out as visitors take in the sights and flavors of Traverse City in late autumn. traversecity.com/tcbw
Mac and Cheese Cook Off | Nov. 7, Charleston, WV
Bring your appetite to Capitol Market’s Mac & Cheese Cook-Off in Charleston. Sample creative takes on the comfort-food classic from local chefs, then vote for your favorite to help crown the People’s Choice winner. This family-friendly event combines delicious bites, community fun and a chance to celebrate the region’s culinary talent. capitolmarket.net
Mary M. Miller Steamboat Supper | Nov. 6 & 13, Louisville, KY
Celebrate the season aboard the Mary M. Miller, one of Louisville’s historic riverboats. This evening cruise with dinner features music from the Derby City Dandies and scenic views of the Ohio River. It’s a unique way to gather with friends or make new ones while enjoying time on the water. belleoflouisville.org
Motor City Comic Con | Nov. 13–15, Novi, MI
This three-day convention welcomes fans of all ages to celebrate their favorite franchises. As the central hub for all things pop culture, Motor City Comic Con invites fans to explore Artist Alley, watch or participate in the cosplay contests and meet favorite actors and comic artists. Families can enjoy the free kids room, where little ones can make crafts. motorcitycomiccon.com
Winter Festival of Lights | Nov. 14–Jan. 10, Niagara Falls, NY
Taking place from mid-November through late January, this annual festival is widely considered one of the most enchanting of the area’s attractions. The festival features captivating displays, fireworks and a total of over 3 million lights. Catch the magical light show “Sparkling Winter Lights” presented by the Niagara Falls Illumination Board. wfol.com
‘A Christmas Story’ Comes Home | Nov. 21–Dec. 30, Hammond, IN
Six animatronic window displays from Macy’s department store in New York City appear in Hammond, Indiana, this holiday season. The displays depict different scenes from the classic holiday movie “A Christmas Story,” which takes place in a fictionalized version of author Jean Shepherd’s hometown of Hammond. Get in the holiday spirit as you gaze at the displays, browse the gift shop and grab a photo with Santa. southshorecva.com
Buffalo Holiday Market | Nov. 27–Dec. 23, Buffalo, NY
Reserve your igloo or plan a visit with Santa Claus for you and your family this winter during the annual Buffalo Holiday Market. This five-week event focuses on bringing a very European Christmas to western New York, featuring crafted foods from the region, such as pierogies, Dutch mini pancakes and more. This year’s market features a variety of vendors selling treats, crafts and artisan works. buffaloholidaymarket.com/
Christmas at the Seiberling | Nov. 28–Dec. 30, Kokomo, IN
This walk-through tour of Kokomo’s Seiberling Mansion kicks off with a lighting ceremony on Nov. 28 that invites guests to tour the house with Santa Claus. Those who can’t make it the first night can tour the home as it dressed up for the holidays during evenings in December. howardcountymuseum.org
DECEMBER
Dutch Winterfest | Dec. 2–6, Holland, MI
This seasonal holiday celebration in downtown Holland fully immerses visitors in a festive winter atmosphere and includes many different holiday favorites to enjoy. With curated tours, ice skating, tastings and more, Dutch Winterfest captures the feel of a European Christmas and helps visitors learn about Dutch holiday traditions. holland.org
Christmas in the Village of Elizabeth | Dec. 4–5, Elizabeth, IL
Nothing beats small-town holiday magic, and during this two-day celebration, there’s plenty of it. Stroll through the idyllic town of Elizabeth as it is decked out for the holidays. Families can enjoy the season kickoff with lights and local cheer throughout the village, creating a Christmas-movie atmosphere. visitgalena.org
Hayes Home Holidays | Dec. 18–19, Fremont, OH
The Rutherford B. Hayes Presidential Library and Museums celebrates the holidays in presidential style. Hosted for just two nights at the Fremont estate of the 19th President of the United States, this experience allows visitors to see the Victorian mansion decorated for the holidays. Learn about Christmas traditions celebrated in the White House by various U.S. presidents. rbhayes.org
Vienna Light Orchestra Tour | Dec. 19, Louisville, KY
Celebrate the magic of the holidays with the Vienna Light Orchestra as it brings its Christmas Tour to Louisville. Set beneath the glow of candlelight, the performance features world-class musicians and vocalists performing beloved seasonal classics in a theatrical show that blends symphonic music, festive decor and timeless holiday tradition. viennalightorchestra.com
First Night Pittsburgh | Dec. 31, Pittsburgh, PA
This free New Year’s Eve party spans 14 blocks of Pittsburgh’s cultural district and invites people of all ages to ring in 2027 together. The First Night party is focused on showcasing the arts of Pittsburgh through live music, dance, theater and more. The party also includes a fireworks display at 8 p.m. and midnight. firstnightpgh.trustarts.org
JANUARY
Fire & Ice Festival | Jan. 30, Bracebridge, ON
Experience the best of a Canadian winter at the Fire & Ice Festival in downtown Bracebridge. This one-day celebration features thrilling snow tubing down the town’s main street, live fire performances, ice sculptures, skating, fireworks and cozy fire pits. Family-friendly activities and local vendors make this tradition a memorable way to embrace the season. facebook.com/fireandicebracebridge
Buckeye Lake Winterfest | Jan. 30, Buckeye Lake, OH
Head to central Ohio and the shores of Buckeye Lake to see if Benny the Bass takes the bait or refuses, predicting an early spring or signifying six more weeks of winter. Buckeye Lake Winterfest offers fun for the whole family with live music, food trucks and even a polar plunge the day after the festivities. escapetobuckeyelake.com
FEBRUARY
Groundhog Day in Punxsutawney | Feb. 2, Punxsutawney, PA
Come and party with Punxsutawney Phil and see if he sees his shadow during the annual Groundhog Day festival in Punxsutawney, Pennsylvania. The day starts at Gobbler’s Knob, where Phil makes his prediction, and notable related events include Lunch with Phil, the Groundhog Ball and the annual Groundhog Banquet. groundhog.org
Illinois PolkaFest | Feb. 5–7, Schaumburg, IL
Since 1988, Illinois Polkafest has welcomed polka fans for a weekend of dancing and performances by top Cleveland-style polka bands. Now led by founder Bob Doszak’s son, Chris, the annual tradition continues in Schaumburg, bringing together fans from across the country for great music and family-friendly fun. illinoispolkafest.com
MARCH
Arnold Sports Festival | March 4–7, Columbus, OH
Featuring over 500 booths of the latest sports equipment, the Arnold Sports Festival returns to Columbus, Ohio, each March. Created by Arnold Schwarzenegger, this year’s event features competitions, entertainment, vendors and plenty of inspiration to ensure attendees walk away feeling fueled up to become their strongest selves. arnoldsports.com
Toronto St. Patrick’s Day Run | March 14, Toronto, ON
Take part in the 2027 Toronto St. Patrick’s Day Run at Evergreen Brick Works, a spring tradition supporting Achilles Canada. Choose from a 5K, 10K or kids 1K and enjoy the scenic route along the Don Valley. Finish with festive Irish music, a celebratory atmosphere and post-race food and drinks. raceroster.com