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 every weekend, for all tastes. Whether you're looking for romantic events, things to do with friends, 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 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 weekends early. This event 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 in The Back Room at Burn 'Em.

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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
• Union Pier Social | 7:00 PM
• The Acorn | 8:00 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
⏰ 12 – 11 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 on two wheels 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, and beloved Fort Wayne duo Bobcat Opossum.

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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 Galien River 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 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

Enjoy a fun-filled day of noteable 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 on the patio.

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📍 Michigan City
⏰ 7:00 – 10:00 PM CT
🎟️ Free

Enjoy good food, and better beer (+ wine & cocktails) while listening to toe-tapping live jazz from Bill Romer & friends.

📍 Local Pour | Sawyer
⏰ 6:00 – 7:30 PM
🎟️ Tickets Required

Learn how to craft Michigan-inspired cocktails while enjoying an evening of spirits, techniques, and local flavors.

📍 Round Barn Tasting Room | Union Pier
⏰ 7:00 PM
💲 Tickets

Get moving with this fun community run and walk series before rewarding yourself with local wine and good company.

📍 The Acorn | Three Oaks
⏰ 7:00 PM
🎟️ Tickets Required

An evening of laughter, entertainment, and bingo with fabulous hosts and prizes.

📍 Kankakee Live at Four Winds Casino | New Buffalo
⏰ 7:30 PM
💲 Free

Join Sunset Coast Country Dancers for a lively evening of line dancing. Beginners welcome!

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📍 Bridgman
⏰ 9:00 AM
📝 Registration Required

Start your morning surrounded by beautiful lavender fields with a relaxing outdoor yoga session.

📍 Guy Foreman Amphitheater | Michigan City
⏰ 12:00 – 8:00 PM CT
💲 Free

Celebrate Juneteenth with music, food, vendors, community activities, and cultural programming throughout the day.

📍 Golden Muse Winery | Baroda
⏰ 5:00 – 8:00 PM
💲 Free

Enjoy live music, wine, and community as Golden Muse hosts an evening Juneteenth celebration.

📍 Dancing Feet Yoga | New Buffalo
⏰ 7:00 PM
📝 Registration Required

Welcome the longest day of the year with a restorative sound healing experience.

• Four Winds Casino | 5:00 PM
• Lake Time Brewing & Spirits | 7:00 PM
• Sonny D's | 7:00 PM
• The Acorn | 8:00 PM
• Live at the Lakefront (Michigan City) | 8:00 PM CT

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📍 Round Barn Estate | Baroda
📅 June 20 – 21
⏰ 11:00 AM – 6:00 PM
💲 Cover Charge

Escape to the islands without leaving Southwest Michigan. Enjoy tropical cocktails, live entertainment, and summer vibes all weekend long.

📍 Sandpiper | Bridgman
⏰ Noon
📝 Registration Required

Create your own beautiful macramé art piece during this hands-on workshop.

📍 Timothy's | Union Pier
⏰ 1:00 – 4:00 PM
🎟️ Tickets Required

Sample an exceptional selection of wines curated by The Wine Sellers during this special tasting event.

📍 Burn 'Em Brewing | Michigan City
⏰ 1:00 – 10:00 PM CT
🎟️ Tickets Required

An all-day celebration of music, art, beer, and creativity at one of the area's favorite breweries.

• Tabor Hill Winery | 2:30 PM
• Round Barn Tasting Room | 3:00 PM
• Round Barn Brewery | 6:00 PM
• Peat's Cider Social | 7:00 PM
• Union Pier Social | 7:00 PM
• The Acorn | 8:00 PM
• Live at the Lakefront (Michigan City) | 8:00 PM CT
• Four Winds Casino | 10:00 PM

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📍 Journeyman Distillery | Three Oaks
⏰ 11:00 AM – 3:00 PM
🎟️ Tickets Required

Treat Dad to a delicious brunch featuring great food, craft cocktails, and a festive atmosphere.

• Red Top Winery | Noon
• Tabor Hill Winery | 2:30 PM
• Lemon Creek Winery | 3:00 PM
• Out There | 3:00 PM
• Shoreline Brewery | 3:00 PM CT

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📍 Friendship Botanic Gardens | Michigan City
⏰ 5:00 PM CT
🎟️ Tickets Required

Take inspiration from the beautiful gardens while learning watercolor techniques from local artists.

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

Acclaimed singer-songwriter Anders Osborne brings an intimate evening of blues, rock, and Americana music to The Acorn.

 

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📍 Tom Cat Tavern | Three Oaks
⏰ 7:00 PM
🎟️ Free

A series of short (5-7 minutes) PowerPoint presentations that will entertain and educate!

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📍 Bridgman
⏰ 9:00 AM
📝 Registration Required

Another opportunity to unwind among the lavender blooms and start your day with intention.

📍 Public Library | Michigan City
⏰ 2:00 PM CT
💲 Free

Join PBS Michiana WNIT and community members for a screening and discussion exploring this important chapter of American history.

📍 Peat's Cider Social | Stevensville
⏰ 4:00 – 10:00 PM
💲 Free

Celebrate the music and culture of the Grateful Dead with themed festivities, live music, and cider.

• Four Winds Casino | 5:00 PM
• Red Top Winery | 5:00 PM
• Peat's Cider Social | 6:00 PM
• Lake Time Brewing & Spirits | 7:00 PM
• Burn 'Em Brewing | 7:00 PM CT
• The Acorn | 8:00 PM
• Four Winds Casino | 10:00 PM

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📍 North Pier Brewing Company | St. Joseph
⏰ 8:30 AM
🎟️ Tickets Required

Adventure seekers can enjoy this scenic 15-mile kayak excursion along Michigan's beautiful shoreline.

📍 St. Joseph
⏰ 12 – 8 PM
💲 Free

Celebrate Pride Month with live entertainment, food, artists, games, and more.

📍 The Sandpiper | Bridgman
⏰ 1:00 PM
🎟️ Tickets Required

Learn the basics of needle felting and create your own handcrafted project.

• Tabor Hill Winery | 2:30 PM
• Round Barn Tasting Room | 3:00 PM
• Round Barn Estate | 3:30 PM
• Chill Hill Winery | 5:00 PM
• Union Pier Social | 7:00 PM
• The Acorn | 8:00 PM
• Live at the Lakefront (Michigan City) | 8:00 PM CT
• Four Winds Casino | 10:00 PM

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📍 Warren Dunes | Sawyer
⏰ 1:00 – 8:00 PM
💲 Free (RSVP Requested)

Explore the beauty of the dunes while learning photography techniques from local creatives.

📍 Welter's Folly & Vickers Theatre | Three Oaks
⏰ 1:30 PM
🎟️ Tickets Required

Enjoy a unique golf-and-movie themed experience featuring the classic comedy Caddyshack.

• Round Barn Estate | 2:30 PM
• Tabor Hill Winery | 2:30 PM
• Shoreline Brewery | 3:00 PM CT
• The Acorn | 8:00 PM

📍 Flourish Books & Plants | New Buffalo
⏰ 4:00 PM
🎟️ Tickets

Create beautiful handmade bookmarks while learning watercolor techniques in a cozy creative setting.

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📍 New Buffalo Township Library
⏰ 6:00 PM
💲 Free

Enjoy a community screening of the classic film followed by discussion and conversation.

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📍 Bridgman
⏰ 5:30 PM
💲 Free

Help celebrate six decades of community service, learning, and connection at the Bridgman Public Library.

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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!

And, check out other on-going activities...

• Our Summer Bucket List
• Unique Activities in Southwest Michigan
• Hikes & Brews
• Local U-Pick Farms and Farmer's Markets (It is Strawberry Season!)
• Summer 2026 Events
• Our Favorite Wineries & Outdoor Dining