Harbor Country Events for Every Season

A locally curated guide to the best of Harbor County and Northwest Indiana

Three Oaks Oaktoberfest 2026

Three Oaks American Legion

The 2026 Oaktoberfest in Three Oaks, Michigan runs from September 18 to September 20 at the Three Oaks American Legion (204 W. Linden St.). The weekend features German food, carnival games, live music, and the Battle of the Brewmasters competition. ...

Sep 20

Burn Em Oktober Fest

Burn ‘Em Brewing 1215 E 2nd Street Michigan City, IN 46360 Starts: 11am ‐ Ends: 8pm

BURN ‘EM OKTOBERFEST Our Oktoberfest party will be rocking in The Taproom AND The Back Room all day Sunday September 20th! The German Band, Inc. will perform 2-5pm. So dust off your Dirndls and Lederhosen and join us for great food, great bier and traditional German music. OH SCHEISSE, our malty Oktoberfest-style Marzen lager brewed with all German malts, hops and yeast will be released on draft and in cans. German inspired food specials will be available all day long. We’ll be open 11am to 8pm CDT. ALL AGES WELCOME ➼ NO COVER ➼ PROST! More Info...

Sep 27

Apple Cider Century

Three Oaks, MI Starts: 7:30

Sunday, September 27, 2026 | Three Oaks, Michigan One of the Midwest's largest and longest-running cycling events, the Apple Cider Century invites riders of all skill levels to experience the beauty of Harbor Country in the fall. Choose from routes ranging from 15 to 100 miles as you pedal through scenic orchards, forests, vineyards, and charming small towns. After the ride, enjoy fresh apples and cider, local vendors, live music, and delicious food while celebrating one of the region's favorite autumn traditions. More Info...

Oct 01

Where's The Witch?

Downtown St. Joseph

Where's the Witch - Downtown St. Joseph Scavenger Hunt! Can you find the witch in all 13 participating locations? More Info

Oct 03

Wetland Wildflower Walk

2300 N. Benton Center Road Benton Center, MI 49022 Starts: 1pm ‐ Ends: 2:30pm

Join us for a wildflower hike through our lowlands. Naturalists will discuss ID tips, pollinators and enjoy the beauty of late season flowers. More Info

Oct 03

Paint your Pet on a canvas with The Mural Artist at Filkins Vineyards

Filkins Vineyards 6991 Ryno Rd Coloma, MI 49038 Starts: 11:30am ‐ Ends: 2:30pm

Join The Mural Artist for a fun and creative Paint your Pet class where you'll turn your favorite furry friend into a one of a kind painting! Whether you're a beginner or an experienced painter, this guided class will walk you step by step through creating a portrait of your pet on canvas. More Info...

Oct 03

Harvest Fest & Chili Walk

DOWNTOWN BUCHANAN Starts: 8am ‐ Ends: 5pm

Mark your calendars for Saturday, October 3, 2026, and join us in beautiful Downtown Buchanan for a day filled with family fun, live entertainment, shopping, delicious food, and community spirit! Featuring the Return of the Famous Chili Walk! More Info ...

Oct 04

World's Best Putter Competition

Journeyman Distillery at The Featherbone Factory 109 Generations Dr, Three Oaks, MI 49128 Starts: 11am ‐ Ends: 3pm

Could you be the World’s Best Putter? Put your skills to the test at Welter’s Folly for Journeyman’s Annual World’s Best Putter Competition. Players will be randomly paired for matchups with the last tee-off taking place at 3pm. More Info...

Oct 10

Beachglass Brewfest

Downtown New Buffalo Starts: 11am ‐ Ends: 6pm

A celebration of Midwest craft culture set in downtown New Buffalo along Whittaker Street — with Lake Michigan as its backdrop. Explore a vibrant lineup of regional breweries, wineries, cideries, and distilleries, paired with local eats, live music, and a relaxed summer vibe. Blending the artistry of brewing with the charm of lakeside living, Beach Glass BrewFest brings together beer lovers, wine enthusiasts, foodies, and friends for an unforgettable Whittaker Street experience. ...

Oct 10

Eden Springs Park Halloween Miniature Train Rides

789 M-139 Benton Harbor 49022 Starts: 5pm ‐ Ends: 8pm

Come enjoy the evening ride and see our Spooky decorations. Halloween-themed miniature train rides in our historic amusement park. Ride and decorations are kid-friendly - some flashing lights. Bring the family and enjoy the holiday ride! More Info...

Oct 10

Fit 4 Fall 5K

200 Broad Street St. Joseph 49085 Starts: 9am ‐ Ends: 10am

LECO’s Annual Fit 4 Fall 5K Run/Walk is returning for another year of family-friendly fun! This year’s race will take place Saturday, October 10, in St. Joseph, Michigan. More Info...

Oct 10

9th Annual Barrel-Aged Brewfest

Journeyman Distillery at the Featherbone Factory 109 Generations Drive, Three Oaks, Starts: 12pm ‐ Ends: 5pm

Sample barrel-aged beers from regional breweries, cast your vote for the People’s Choice Award, browse the silent auction, and enjoy an afternoon of live entertainment while making a meaningful impact. Whether you’re a dedicated craft beer enthusiast or simply looking for a fun day with friends and family, Barrel-Aged Brewfest is one of Southwest Michigan’s favorite fall traditions. More Info...

Oct 17

2026 Spooktacular Market

301 State Street St. Joseph 49085 Starts: 11am ‐ Ends: 4pm

An outdoor Spooktacular Market from 11:00a-4:00p! This event is part of the Downtown Spooktacular. More Info

Oct 17

Harvest Festival 2026

Stovers Farm Market & U-Pic - 7837 US Highway 31, Berrien Springs, MI, Starts: 10am ‐ Ends: 3pm

Join us for this year's Harvest Festival at Stover's U-Pick Farm on October 17th from 10:00-3:00! There will be 30 artisan vendors, food trucks, chili cook-off and live music preformed by Aaron Conley! This is a family friendly event, bring your kids to have some fun on the farm while you get some shopping done from local vendors. More Info...

Oct 17

2026 Downtown Spooktacular

301 State Street St. Joseph 49085 Starts: 11am ‐ Ends: 4pm

Halloween-themed event in downtown St. Joe featuring a variety of events, including a hayride through downtown, a Spooktacular Market, a pumpkin patch, magic shows, a Spooktacular Costume Parade, a pumpkin carving display and demo, Spooky Lighthouse Tours, downtown decorations, etc. More Info...

Oct 18

Haunted Trails

Friendship Gardens, 2055 E US Highway 12, Michigan City, IN Starts: 3 ‐ Ends: 6

Get into the Halloween spirit with an afternoon of family-friendly fun! Everyone is encouraged to wear their Halloween costumes while exploring a festive path through the Gardens with stops at the playground and woodland meadow for games, activities, and candy. The afternoon includes cider, storytellers, a bonfire, and a food truck. More Info...

Oct 25

Simply Unique Market

Berrien County Fairgrounds - 9122 US-31, Berrien Springs Mi Starts: 10am ‐ Ends: 4pm

Each market features a unique mix of between 100-150 different handcrafters, artisans, boutiques, food trucks and more including unique and fun entertainment. The markets are rain or shine events with free parking and just $5 entry per person, under 12 is free. More Info...

Oct 30

Murder Mystery Dinner: A Masquerade at the Featherbone

Journeyman Distillery, 109 Generations Drive, Three Oaks, MI 49128 Starts: 6pm

Dress up for an evening of mystery, cocktails and clues at Journeyman Distillery’s historic Featherbone Factory in Three Oaks. Guests will enjoy a chef-crafted dinner while becoming part of an interactive murder mystery, interviewing suspects, solving puzzles and working together to uncover the killer. Cocktail attire, evening gowns, tuxedos and masquerade masks are encouraged. More Info...

Oct 31

Halloweekend at Round Barn Winery & Estate

10983 Hills Rd, Baroda, MI 49101

Celebrate spooky season in Southwest Michigan wine country with Halloweekend at Round Barn Winery & Estate! This festive weekend marks the grand finale of our Jammin’ in the Vineyard live music series More Info...

Nov 07

Journeyman Autumn Artisan Market

Journeyman Distillery at The Featherbone Factory 109 Generations Dr, Three Oaks, MI 49128 Starts: 10am ‐ Ends: 5pm

Head to Journeyman Distillery’s historic Featherbone Factory in Three Oaks for its annual Autumn Artisan Market. Browse handcrafted goods and unique gifts from talented local artists and makers while enjoying a craft cocktail. Make a day of it with brunch at Staymaker Restaurant and a stop at the Journeyman shop. More Info...

Nov 20

St Joe Luminary

Downtown St Joseph, MI Starts: 5pm ‐ Ends: 8pm

Luminarias will light your way as you stroll through and explore downtown St. Joseph from 5:00p-8:00p during Luminary! Participating locations invite you to eat, shop, drink and be merry while you enjoy this charming lakeside town. More info...

Nov 23

Thanksgiving Turkey Pickup

Farmette 18439 US HWY 12, NEW BUFFALO, MI 49117

Pre-order your pasture-raised turkey with Willowbrook Farms and pick it up at farmette. More Info...

Nov 26

Thanksgiving Turkey Walk

Friendship Gardens, 2055 E US Highway 12, Michigan City, IN Starts: 11am ‐ Ends: 1pm

Start your Thanksgiving off right with fresh air and time in the Gardens. Guests are invited to walk the trails and enjoy the peaceful beauty of the season with family and friends. Join us from 11 am – 1 pm CDT for a relaxed and family-friendly way to begin the holiday! This event is free for all attendees. More Info ...