Road trip-worthy happenings on the south Michigan shore

Our curated picks for the many ways to celebrate this special season on the lakeshore. Explore festivals, u-picks, bike tours, and a locally legendary Halloween dance party.

Williams Orchard

Thursdays-Sundays | September-October | Rolling Prairie, IN

What could be more quintessentially autumn than apple picking? Set in the rolling hills of the Hesston Corridor, Williams 135-acre orchard is your harvest season fantasy come true. Weekends feature wagon rides and a limited supply of pies, doughnuts, taffy apples and cider, and be sure to stop by the petting zoo. The baby goats and miniature donkeys are crazy cute. $5 (weekdays free)

Learn More | Explore Williams

Dinges Fall Harvest

September 28-October 31 | Three Oaks, MI

Every autumn, the Dinges’ charming farmstead transforms into a spooky, silly spot for pumpkin patch adventure. Go for the amazing selection of pumpkins and gourds (u-pick or pre-pick), stay for the old-school family fun and Halloween-inspired attractions.

Learn More | Explore Dinges

Granor Farm Dinners & Brunch

Fridays-Sundays | Three Oaks, MI

Family-style meals prepared with minutes-fresh produce from Granor’s lovely organic farm. Take a tour, shop the farmstand, then sit down to a truly memorable meal prepared by chef Abra Berens. Without a doubt, the most down-to-earth, engaging, and delicious dining experience in the region. $45-85

Reserve NowExplore Granor

Live Music at Dablon Winery

Fridays and Sundays| September-November | Sundays in December | Baroda, MI

Dablon’s inviting fireside tasting room and vineyard-view patio are among our favorite spots to enjoy a Lake Michigan Shore vintage. A live acoustic soundtrack is icing on the cake.

Learn More | Explore Dablon

The top of the white round barn against a blue sky at Round Barn Winery in Baroda, Michigan.

Jammin in the Vineyard

September 21, 22, 28, 29 | October 13, 19, 20, 26 | November 10 | Baroda, MI

The best party on the wine trail continues through autumn at Round Barn. Guests enjoy live music, food trucks, wine, beer, and spirits and plenty of space to dance and relax. The friendly folks here have absolutely mastered this scene. $5

Learn More | Explore Round Barn

Three Oaks Wurstfest

September 21 | Three Oaks, MI

Lederhosen are admired, but not required, at this fun-loving community celebration. Originally conceived to commemorate Driers Meat Market’s 100-year anniversary in 2013, Wurstfest has become a fall tradition with craft beer, wine and cider from more than 40 regional makers, live music, a classic car show, kids activities, and craft and food vendors – including ‘liverbest’ champions, Driers.

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Vintage black & white photographs at Blue Moon Vintage Market in Three Oaks, Michigan.

Blue Moon Vintage Market

September 27-29 | October 25-27 | November 29-December 1 | December 13-15 | Three Oaks, MI

An expansive monthly market featuring vintage, primitive and architectural treasures sourced by pickers across the country. Artfully staged with new finds every month, Blue Moon has earned a devoted fan following of collectors, designers, and diy-ers.

Learn More | Explore Blue Moon

Apple Cider Century

September 29 | Three Oaks, MI

Experience the midwest’s most popular century bike tour. From hard-core, kit-wearing packs to families with little ones fresh off training wheels, ACC offers fully-supported 15, 25, 37, 62, 75 or 100 mile tours through the stunning Lake Michigan shore countryside.

Learn More | Explore ACC

A nighttime view of The Acorn's entrance in Three Oaks, Michigan.

The Accidentals at The Acorn

October 5 | Three Oaks, MI

After over a thousand live shows including an enthusiastic SXSW debut, young northern Michigan natives The Accidentals perform for the first time on The Acorn stage. Genre-hopping and witty with significant musical chops thanks to years of classical training, this intimate venue will be a fitting showcase for this diverse and talented band. $30-50

Get Tickets | Explore Acorn

New Buffalo Harvest  & Wine Festival

October 12 | New Buffalo, MI

This annual lakefront celebration is more than the name might suggest. Yes, a fine representation of Lake Michigan Shore wines, but also regional beers, ciders and sodas. Tasty food trucks. A craft, farmers and producers market. Kids activities. And, of course, music! A community gathering for visitors and locals alike, it’s a day-into-night event full of smiles and gratitude for all the region provides. $5

Learn More | Explore the Fest

Photo Courtesy of Lakeside Inn

Storehouse 011 at Lakeside Inn

October 19 | Lakeside, Michigan

An intimate house concert series, Storehouse 011 features a first-time partnership with the historic Lakeside Inn to present Meg Baird and Mary Latimore in concert. The duo will perform their collaborative work ‘Ghost Forests’ – compositions on harp, guitar, synth and voice – sure to add a layer of intrigue to the storied walls of the inn. Guest are encouraged to bring a potluck dish to share before the show. $20

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Journeyman Barrel Aged Brewfest

October 19 | Three Oaks, MI

Explore single-batch, barrel-aged beverages produced by 30 regional breweries, wineries, and mead/cideries as they compete for bragging rights and the coveted Golden Barrel Trophy.  A benefit for Journeyman’s non-profit Islay’s Barrel, this event draws a committed group of craft brew fans every year. $40-$75

Get Tickets | Explore Journeyman

Journeyman Halloween Dance Party

November 1 | Three Oaks, MI

Always a sell-out, Journeyman’s  annual Halloween party features spooky-themed cocktails, DJ, and a high-stakes costume competition with prizes. The historic factory-turned-distillery is a perfect setting for a night of alter-ego fun. Tickets sold in advance only. $10

Get Tickets | Explore Journeyman

Journeyman Artisan Market

November 23-24 | Three Oaks, MI

Journeyman welcomes 75 regional artisans to its historic 19th century factory space just in time for the holiday gift-giving season. Take the chill off with a handcrafted cocktail while browsing the wares and chatting up makers. It’s a delightfully low-key holiday kickoff.

Learn More | Explore Journeyman

Photo Credit Jamie & Eric Photography

Granor Farm Thanksgiving Pop-up Market

November 24 | Three Oaks, MI

If the intense pre-Thanksgiving grocery shopping scene harshes your holiday mellow, head to the farm for a delightful alternative totally worth the road trip. In addition to the abundance of Granor’s organic vegetable harvest, you’ll find Gunthorp Farms pasture-raised turkey (available for pre-order), charcuterie and cheese from Forage & Foster, sourdough bread from The Elder BreadViolet Sky single origin chocolate, wine tasting with P. & E. Bottle ShopRed Arrow Roasters small-batch coffee, organic cider and apples from Earth First Farms, and fresh-cut flowers from Field & Florist. Everything you need from organic, sustainable, and local producers! We guarantee, you’ll still be smiling as you pack up the car.

Learn More | Explore Granor

The entry of Goods & Heroes in Three Oaks, Michigan.

Three Oaks Snowflake Stroll

November 30 | Three Oaks, MI

The merchants of downtown Three Oaks host an annual holiday kickoff brimming with good cheer. From 12-8pm, shops and eateries offer treats and drinks, great conversation, and unique gifts along with a chance to chat up Santa and carol with The Harbor Country Singers. New this year, Three Oaks Social Club will host a special exhibition of small, gift-able works by artists Elizabeth Coyne and Andrea Federle Busci, as well as a demo with chef and cookbook author Abra Berens. The best kind of shop small experience, we especially love to stroll at dusk in the pre-dinner hours.

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Lauren Manoogian / The Elder Statesman Holiday Trunk Show at AP

November 30-Dec 1 | Dec 7-8 | Lakeside, MI

A coast-to-coast exploration of luxury knitwear designed by Brooklyn-based Lauren Manoogian and LA-based The Elder Statesman. Curated and merchandised by AP’s talented Ariane Prewitt, we can’t wait to see the visual conversation between these alternately soft and outspoken designs.

Explore AP

Dudeck’s Pine Country

November 29-December 22 | Rolling Prairie, IN

An 80-acre Christmas tree farm with a special gift for holiday cheer. Hunt evergreen-covered hills by foot or horse-drawn wagon, chat with Santa, and shop fresh handcrafted greenery and rustic decor. The place is as wonderful as the people.

Learn More | Explore Dudeck’s

For a complete list of area events, visit our friends at Harbor Country Chamber of Commerce.

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