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Things To Do in Harbor Country This May

🌷 May 2026 Events in Harbor Country

Live Music, Wine Weekends & Lakeshore Fun

May is a beautiful time to visit Harbor Country and Southwest Michigan. The flowers are in full bloom, farmers markets return for the season, patios fill with live music, and communities across the lakeshore come alive with spring celebrations.

From Kentucky Derby parties and Mother’s Day markets to winery weekends, outdoor adventures, concerts, and Memorial Day festivities, there’s something happening every weekend near Garden Grove Inn in Union Pier.

Whether you're planning a romantic getaway, girls’ wine weekend, relaxing escape, or a spontaneous spring road trip, Garden Grove Inn is the perfect home base for enjoying everything Harbor Country has to offer this month.


🌼Early-Mid May Events

πŸ“… Friday, May 8

πŸš—πŸŽΈ Cars, Guitars & Cider
πŸ“ Peat’s Cider Social β€’ Stevensville
πŸ•• 6 PM β€’ πŸ’² Free
Classic cars, live music, and local cider make for the perfect spring evening.

🎀 Sixteen Candles Live at The Acorn
πŸ“ Three Oaks
πŸ•— 8 PM β€’ 🎟 Tickets
A nostalgic night of live music at one of Harbor Country’s favorite venues.


πŸ“… Saturday, May 9

β˜•πŸš˜ Cars & Coffee at Oaks Eatery
πŸ“ Three Oaks
πŸ•£ 8:30 AM – 11 AM β€’ πŸ’² Free
Coffee, breakfast, and cool cars to kick off the weekend.

πŸ›οΈπŸŒΈ Mother’s Day Market
πŸ“ American Legion Post 518 β€’ New Troy
πŸ•™ 10 AM – 3 PM β€’ πŸ’² Free
Browse handmade gifts, baked goods, dΓ©cor, and local artisan vendors.

πŸ›οΈπŸ’ Mother’s Day MarketΒ 
πŸ“ Downtown Stevensville
πŸ•™ 10 AM – 4 PM β€’ πŸ’² Free
Enjoy shopping, spring vendors, flowers, treats, and downtown charm.

πŸ«–πŸ›οΈ Mother’s Day Tea at Barker Mansion
πŸ“ Michigan City
πŸ• 1 PM β€’ 🎟 Tickets
Celebrate Mom with elegant tea service inside a historic mansion.

πŸ₯ΎπŸŒΏ Ecologist Hike at Ambler Flatwoods
πŸ“ Michigan City
πŸ• 1 PM β€’ πŸ“‹ RSVP Requested
Explore spring wildflowers and natural beauty on a guided educational hike.

🎢 UB40 Featuring Ali Campbell
πŸ“ Silver Creek Event Center at Four Winds β€’ New Buffalo
πŸ•˜ 9 PM β€’ 🎟 Tickets
A huge concert event featuring reggae favorites and classic hits.

πŸ·β˜€οΈ Round Barn Sangria Party
πŸ“ Round Barn Winery
πŸ“… May 9 & 10 β€’ πŸ•š 11 AM – 6 PM β€’ πŸ’² Cover Charge
Spend the weekend sipping sangria and soaking up vineyard views.


πŸ“… Sunday, May 10

🧺🌻 Bridgman Open Air Market Opening Day
πŸ“ Bridgman
πŸ•˜ 9 AM – 3 PM β€’ πŸ’² Free
Fresh produce, flowers, baked goods, handmade items, and local favorites return for the season.


πŸ“… Tuesday, May 12

🐱🍸 Meow & Tell at Tom Cat Tavern
πŸ“ Three Oaks
πŸ•– 7 PM β€’ πŸ’² Free
A quirky and entertaining evening for those who appreciate a good tale.


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πŸ“… Saturday, May 16

🐢🌳 Dog Days at Fernwood
πŸ“ Buchanan
πŸ•˜ 9 AM – 11 AM β€’ πŸ’² Cover Charge
Bring your furry friends for a fun morning outdoors.

πŸ·πŸƒ World’s Okayest Wine Run
πŸ“ Tabor Hill Winery
πŸ•š 11 AM β€’ πŸ’² Free
Part fun run, part wine party β€” and all Harbor Country fun.

πŸŽΆπŸ›οΈ SIP! Buchanan
πŸ“ Downtown Buchanan
πŸ•‘ 2 PM – 6 PM β€’ πŸ’² Free
Live music, dancing, drinks, farmers markets, shopping, and community celebrations.

πŸ‘πŸ›’ Watermark Yard Sale
πŸ“ Stevensville
πŸ•š 11 AM – 4 PM β€’ πŸ’² Free
A community-wide treasure hunt filled with bargains and hidden gems.

πŸ₯–πŸŒ· Skip’s European Farmers Market Opening Day
πŸ“ New Buffalo
πŸ•˜ 9 AM – 3 PM β€’ πŸ’² Free
One of Harbor Country’s most beloved seasonal markets returns.


πŸ“… Sunday, May 17

🎸🍺 Jake Diggity & Sincopado Live
πŸ“ Shoreline Brewery β€’ Michigan City
πŸ•’ 3 PM – 7 PM β€’ πŸ’² Cover Charge
Enjoy live music, craft beer, and lakeshore vibes.

🎀🍻 Aaron James Wright Live at Haymarket Taproom
πŸ“ Bridgman
πŸ•• 6 PM β€’ πŸ’² Free
An easygoing evening of acoustic music and local brews.

πŸŽ™οΈβœ¨ Open Mic Night at The Acorn
πŸ“ Three Oaks
πŸ•– 7 PM β€’ 🎟 Tickets
Discover local talent in one of the area’s favorite performance spaces.


πŸ“… Monday, May 18

β˜€οΈπŸΉ SideYard Summer Kick-Off Party
πŸ“ Sawyer
πŸ•“ 4 PM β€’ πŸ’² Free
Celebrate the unofficial start of summer with music, drinks, and outdoor fun.

🎷🍺 Jazz Night at Shoreline Brewery
πŸ“ Michigan City
πŸ•– 7 PM β€’ πŸ’² Free
Relax with live jazz and great local beer.


Memorial Day Weekend Events

πŸ“… Friday, May 22

🎢🌊 Terrapin Flyer Live at the Lakefront
πŸ“ Michigan City
πŸ•— 8 PM β€’ 🎟 Tickets
An energetic lakeside concert experience near Lake Michigan.


πŸ“… Saturday & Sunday, May 23–24

🎨🍷 Memorial Weekend Wine & Art Festival
πŸ“ Lemon Creek Winery
πŸ•› 12 PM – 6 PM β€’ πŸ’² Free
Wine tastings, local artists, food vendors, and live entertainment all weekend long.


πŸ“… Saturday, May 23

🎡🍷 Live at the Pier featuring Paolo Apuli
πŸ“ Round Barn Tasting Room β€’ Union Pier
πŸ•’ 3 PM – 6 PM β€’ πŸ’² Free
Enjoy wine, live music, and spring sunshine just minutes from Garden Grove Inn.

πŸŽ€πŸ‡ Shanneen Live at Golden Muse Winery
πŸ•” 5 PM – 8 PM β€’ πŸ’² Free
Relax with live music and vineyard views.

🎩✨ An Evening of Interactive Magic & Mystery
πŸ“ Solarium β€’ Stevensville
πŸ•— 8 PM β€’ 🎟 Tickets
A unique experience filled with good beer, magic and surprises.


πŸ“… Sunday, May 24

πŸ›₯️🎢 Sunday Funday Yacht Rock Party
πŸ“ St. Julian Winery β€’ Union Pier
πŸ•‘ 2 PM – 5 PM β€’ πŸ’² Free
Live yacht rock favorites, wine, and holiday weekend fun.

🎸🍷 Dylan Raymond Live at Solasta Winery
πŸ•” 5 PM β€’ πŸ’² Free
An intimate live music performance to close out the holiday weekend.


πŸŒ… End-of-May Events

πŸ“… Saturday, May 30

🎢🌟 An Evening with Michael McDermott
πŸ“ The Acorn β€’ Three Oaks
πŸ•— 8 PM β€’ 🎟 TicketsΒ 

An unforgettable performance from acclaimed singer-songwriter Michael McDermott.


πŸ“… Sunday, May 31

🎸🍺 Janky Limo Live at Shoreline Brewery
πŸ“ Michigan City
πŸ•’ 3 PM – 7 PM β€’ πŸ’² Cover Charge
Finish the month with live music, local beer, and great Harbor Country energy.


πŸ–οΈ Plan Your Harbor Country Escape

May is the perfect time to enjoy Harbor Country’s wineries, beaches, charming downtowns, farmers markets, and live entertainment before the busy summer season arrives.

Garden Grove Inn in Union Pier is conveniently located near many of the area’s top events, wineries, breweries, restaurants, and Lake Michigan beaches β€” making it the perfect destination for your spring getaway.


🎁 Looking for the Perfect Gift?

Garden Grove Inn gift certificates are available online, in any denomination and make wonderful gifts for Mother’s Day, graduations, birthdays, anniversaries, or future weekend getaways.

🧑 Additional gift ideas include:

  • β˜• Hand-thrown mugs β€” $40
  • πŸ₯‚ Logo drinking glasses β€” $12
  • 🍷 Logo wine glasses β€” $12
  • πŸ‘• Garden Grove Inn t-shirts β€” $25

πŸ“§ For more information, contact: hillary@gardengroveinn.com

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