Cozy adventures for your autumn agenda
Pumpkin patch magic. Chili cookoffs. Oktoberfest, farm dinners, and cozy craft meet-ups. If you’re craving peak autumn vibes, Harbor Country’s fall events lineup checks the boxes. We’ve curated a list of some of our favorites to help you plan. Bring a sweater and your taste for adventure—or hot apple cider.
APPLE CIDER CENTURY BIKE TOUR
September 27 | Harbor Country
For everyone from hardcore, kit-wearing packs to families with little ones fresh off training wheels, ACC is the Midwest’s most popular century bike tour. Offering fully supported routes of 15–100 miles through lovely Lake Michigan shore countryside, the ride’s a 52-year tradition for visitors and locals alike. $75 (kids under 12 ride free)
YarnHaus Day Camp at Goods & Heroes
September 28 | Three Oaks
Start cozy season with this day-long intensive for knitters, crocheters, and fiber-arts freaks. YarnHaus plays host to expert Midwestern knitters including Michael Fleming of Minnesota’s Blue Sky Fibers, Jamie Lewis of Traverse City’s Fresh Coast Fiber Festival, and Rick Fuller of Bridgman’s Hoof to Hanger Fiber Mill. Bring your needles and a notebook: The YarnHaus crew shares tips and tricks for colorwork, mosaic knitting, scrap-yarn techniques, granny squares, and more. $275
Tickets | Explore Goods & Heroes
Up on a Hill Music Festival
September 2, 16, & 30 | New Buffalo
A poolside patio and garden event tent set the stage for Up on a Hill’s inaugural season. Experience three Midwest artists at Apple Blossom Resort’s private 18-acre estate: Elizabeth Moen (Sep 2), Big Sadie (Sep 16), and Liam Kazar (Sep 30). Programmed by celebrated local musician and composer Erik Hall, be sure to arrive early for food, drinks, and DJ sets. All in support of Neighbor by Neighbor, a nonprofit providing life essentials to those in need. $35–$75
Tickets | Explore Apple Blossom
Sourdough Club: Pizza at Granor Farm
October 1 | Three Oaks
Dough like a pro with this deep dive into sourdough pizza crust making, led by Granor’s head baker and house fermentation expert, Jill Morgan. Though the curriculum is thorough—touching on mixing, fermenting, shaping, stretching, and wood-fired baking—the method is casual. Class kicks off with a pizza and wine party in the Granor Kitchen, where you’re encouraged to bring all your ‘burning sourdough questions.’ $75
Wreaths & Wine Workshop at Granor Farm
October 2 | Three Oaks
Craft a souvenir of Harbor Country’s endless summer with a DIY wreath of dried flowers harvested from organic fields, just steps away. Materials include naturally preserved sunflowers, dahlias, zinnias, amaranth, and more varieties from the farm’s fresh-cut flower program. Sip Granor wines, zone out with blooms, and shape your own work of everlasting beauty. $96
Oktoberfest at Seedz
October 3 | Union Pier
Forget Munich: German-style lagers, pilsners, and bocks are flowing at Seedz, a small-batch brewer and winner of USA Today’s ‘Best New Brewery in the United States’ prize. On the brewery’s sun-dappled biergarten and grounds, the sixth annual Oktoberfest is a Harbor Country-fied celebration of European-style brewing, Michigan-grown ingredients, and the art of the frothy ‘slow pour.’ Seedz ’26 Oktoberfest bier, German fare, and live music are all on the menu. Lederhosen and dirndls optional but encouraged.
$25–$40
Pasta Club: Traditional Techniques at Granor Farm
October 8 | Three Oaks
With tips and tricks passed down by her Italian nonna and nonno, Julie Morelli of Nourishing Notes teams up with Granor’s head baker, Jill Morgan, to teach the basics of traditional pasta making. Push up your sleeves and learn the art of mixing, kneading, and rolling pasta with an old-fashioned Italian mattarello rolling pin. Granor wines and plates of fresh spaghet made with Granor’s organic flour included. $75
Not-Chili Cookoff at Granor Farm
October 10 | Three Oaks
The humble bean is the star of this veggie-chili cookoff and all-you-can-eat lunch on the farm. This year’s competitors rep some of Harbor Country’s standout kitchens. Cooks from Viola Café, SideYard, Tapa Taco, and Granor throw down for the trophy: a comically giant silver spoon. Entry covers bottomless bowls of bean chili, dunkable bread, and a donation supporting food security for locals in need. $25
Dead Inside DJs at Out There
October 11 | Sawyer
Calling all Deadheads, wine geeks, and seekers of chill Sunday hangs: Out There wine bar hosts a special all vinyl, all live-recorded Grateful Dead set by Chicago’s Dead Inside DJs. Come for curated wines, deep Dead cuts, and collectible merch. Dead Inside rolls with their own Stealie-inspired gear.
Learn More | Explore Out There
Circling Center: The Descent of Venus at Inner Freedom Farm
October 18 | Buchanan
A dreamy afternoon of delving into astrology while getting close to horses and their healing powers. Elizabeth Carden of Inner Freedom co-leads the experience with astrology and tarot reader Julie Kelton of High Low Tarot. Like many of Inner Freedom’s events, this one’s hard to explain but easy to feel. Embrace the mystery and soak up the pasture’s ineffable magic during peak autumn. $80–$160
Tickets | Explore Inner Freedom
Maker’s Halloween Meet-Up at Handmade Studio
October 24 | Sawyer
At this Halloween party-slash-craft night, creative spirits gather for a night of snacking, chatting, and low-pressure making. An artist-run space, Handmade’s an inviting hub for all skill levels and media, with a Riso printer, darkroom, kiln, screen-printing rig, and a plethora of hand-making tools on site. Bring your own work in progress or try one of Handmade’s (spooky) supplied crafts.
Granor Farm Dinners
Select Fridays & Saturdays | Three Oaks
Set in a stunning dine-in greenhouse, Granor Farm’s popular ticketed dinner series is a treat. Tour the farm before settling in for a multicourse, Granor-grown organic meal celebrating the expansive food culture of Southwest Michigan. Because menus are never repeated, it’s a once-in-a-lifetime experience every time. Tickets often sell out, so plan early for the best chance at seats. $175+
Goat Hikes at Verdant Hollow Farm
Saturdays | Buchanan
A guided, hour-long walk through gardens, pasture, hardwood forest—and yes, hollow—with the farm’s goat herd as your companions and ambassadors. Next level for any nature (and baby-goat video) lover, it’s a delightfully simple way to explore a beautiful place with its adorably engaging residents. Ages 5 and up. $25
Tickets | Explore Verdant Hollow
THROWBACK THURSDAYS AT VICKERS THEATRE
Thursdays | Three Oaks
Vickers’ historic mainstreet movie house hosts a weekly screening of vintage blockbusters worthy of leaving your home screen. On the roster: Paris Blues, The Third Man, and more forever favorites. Get a hot, real buttered popcorn and a glass of wine and enjoy the show.
Fall Harvest at Dinges Farm
Through October 31 | Three Oaks
The quintessential spot for pumpkin picking and old-school fun, the Dinges farmstead is where beloved fall traditions grow like squash vines. Think hayrides, games, a corn maze, and kid-friendly Halloween attractions. Plus gourds, pumpkins, and squash in heirloom varieties and colors to make front porches look perfectly autumnal.
Check back often! New events are added as they’re announced.
words Lena Singer, Sylvie Darling, Collette DiJohn Kemper
updated September 9, 2026
