June kicks off summer with a bang, and there is no shortage of events in Harbor Country and Southwest Michigan. Wineries and breweries are buzzing with activity, outdoor events fill the calendar, and there is live music nearly every day of the week. Whether you're looking for family-friendly activities, wine weekends, dancing, theater, community celebrations, or unique local experiences, you'll find plenty to enjoy near Garden Grove Inn in Union Pier, Michigan.

Here are some of our favorite events happening throughout Harbor Country, New Buffalo, Three Oaks, Sawyer, Baroda, Bridgman, Buchanan, St. Joseph, and Michigan City this June.

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📍 Shoreline Brewery | Michigan City
⏰ 6:00 – 9:00 PM CT
💲 Free

Try your hand at bocce or cheer on local players during this fun monthly gathering. Open to all skill levels and a great way to meet people.

📍 Journeyman Distillery | Three Oaks
⏰ 4:00 – 8:00 PM
💲 Free

Browse local vendors, enjoy food and drinks, and kick off your summer weekend early. This community favorite takes place every Thursday throughout the season.

📍 Burn 'Em Brewing | Michigan City
⏰ 8:00 PM
🎟️ Tickets Required

Enjoy an evening of unpredictable laughs and craft beer at one of Michigan City's favorite breweries.

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📍 Dunes Theater | Michigan City
⏰ 7:00 PM CT
🎟️ Tickets Required

The Dunes Theater opens its season with the classic thriller-comedy Deathtrap. Check the theater schedule for additional performances throughout June.

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If you're looking for live music, Saturdays are packed with options:

• Red Top Winery | 2:00 – 5:00 PM
• Round Barn Estate | 12:00 – 6:30 PM
• Round Barn Tasting Room (Union Pier) | 2:30 – 5:30 PM
• Tabor Hill Winery | 2:30 – 5:30 PM
• Dablon Vineyards & Winery | 3:00 – 5:00 PM
• Golden Muse Winery | 5:00 – 8:00 PM
• SideYard | 7:00 PM
• Sonny D's | 7:00 PM
• The Acorn | 8:00 PM
• Union Pier Social | 7:00 PM

📍 Round Barn Brewery & Public House | Baroda
⏰ 7:00 PM
🎟️ Tickets Required

National touring comedian Derek Richards brings his sharp wit and hilarious storytelling to Round Barn.

📍 Section House | Sawyer
⏰ Noon – 11:00 PM
🎟️ Tickets Required

Whether you're an experienced dancer or a beginner, enjoy workshops, lessons, and a full evening of country dancing.

📍 The Library | Three Oaks
⏰ Noon
💲 Free

Learn about local baseball history from the Biggest Little Baseball Museum during this engaging community presentation.

Skip’s European Farmers Market 

📍 Skip's | New Buffalo
🕘 Saturday & Sunday, 9 AM - 3 PM
💲 Free

One of Harbor Country’s most beloved seasonal markets takes place just up the road from the Inn Saturdays & Sundays all summer long.

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📍 Sawyer
⏰ 9:00 AM – 1:00 PM
🎟️ Registration Required

Explore scenic Harbor Country roads before enjoying a delicious brunch and community gathering.

📍 Round Barn Winery & Estate | Baroda
⏰ 11:00 AM – 6:00 PM
🐾 Cover Charge

Bring your four-legged friends for a day of wine, outdoor fun, and pet-friendly activities.

📍 Commune + Market | Three Oaks
⏰ 3:00 – 6:00 PM
🎟️ Tickets Required

Celebrate Pride Month with music, dancing, and community.

📍 River Saint Joe | Buchanan
⏰ 5:00 – 7:00 PM
💲 Cover Charge

Dance the evening away along the riverfront. This recurring event takes place every Sunday throughout the summer.

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📍 School of American Music | Three Oaks
⏰ 6:30 PM
💲 Free

Join the Harbor Country Singers for a fun and uplifting evening of patriotic favorites.

📍 Various Harbor Country Locations
⏰ 6:00 PM
🎟️ Tickets Required

One of Harbor Country's most unique fundraising events. Guests enjoy a progressive dinner while discovering surprise locations throughout the evening.

📍 The Acorn | Three Oaks
⏰ 8:00 PM
🎟️ Tickets Required

An evening of exceptional bluegrass and Americana music from Grammy-winning fiddler Jason Carter.

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📍 Bridgman
⏰ 9:00 AM
🎟️ Registration Required

Start your day with a peaceful yoga session surrounded by blooming lavender fields. Offered Fridays throughout the summer.

📍 New Buffalo Boat Launch
⏰ 3:00 PM
🎟️ Registration Required

Celebrate Pride Month with a colorful paddle on the water alongside friends and community members.

📍 Peat's Cider Social | Stevensville
⏰ 6:00 – 9:00 PM
💲 Free

Classic cars, live music, and hard cider make for a perfect summer evening.

📍 Three Oaks
📅 June 12 – 14
💲 Free

The beloved 74th Annual Flag Day Weekend returns with a full schedule of parades, live music, food, family activities, and community traditions. Check event organizers for the complete lineup.

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📍 Tabor Hill Winery | Baroda
⏰ Noon – 7:00 PM
💲 Free Admission

Spend the afternoon sipping rosé, enjoying vineyard views, and celebrating summer.

📍 Haymarket Brewery | Bridgman
⏰ 10:30 AM – 6:00 PM

🎯 Registration Required to Play
👀 Free to Watch

Competitive bocce, food, drinks, and plenty of community fun.

📍 Buchanan
⏰ 1:00 – 10:00 PM
💲 Free

One of the region's most popular music festivals featuring an impressive lineup of jazz and blues performers.

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📍 Buchanan
⏰ 2:00 – 5:00 PM
🎟️ Tickets Required

Celebrate summer surrounded by beautiful gardens, refreshments, and nature.

📍 Shoreline Brewery | Michigan City
⏰ 3:00 – 6:00 PM CT
💲 Cover Charge

Enjoy live music, local brews, and a relaxing Sunday afternoon.

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With winery events, outdoor recreation, live music, Pride celebrations, community festivals, theater performances, and family-friendly activities happening throughout June, there's no time like the present to visit Harbor Country.

Garden Grove Inn is conveniently located in Union Pier, putting you close to all the best events in New Buffalo, Three Oaks, Sawyer, Baroda, Bridgman, Buchanan, St. Joseph, and Michigan City. Book your stay and make a summer weekend of it!

Check back for new events each month!