Things to do in the Straits this weekend: Highlands Harvest Fest and Gypsy Fall Fest

PETOSKEY, Mich. — The Straits weekend stacks a paid resort harvest party in Harbor Springs, a free distillery fall festival in Petoskey and a free scenic drive along M-119 from Mackinaw City.

The Highlands Harvest Fest: The Highlands Resort, 600 Highland Road in Harbor Springs, hosts the fest from noon to 4 p.m. Saturday, Oct. 17, according to the Petoskey Area Visitors Bureau listing. Organizers list face painting, cookie decorating, burlap sack racing, pumpkin games, yard games, cider and donuts, Short’s Brewing and Carbliss tastings, a live DJ and a stein-hoisting contest. Tickets are $30 per person; season passholders, lodging guests and children 5 and under are free, the listing says. Pets are welcome.

Fall Fest at Gypsy Distillery: Gypsy Distillery, 5251 Charlevoix Avenue in Petoskey, runs its annual Fall Fest from noon to 6 p.m. Sunday, Oct. 18, the distillery’s events page says. Admission is free. Planned offerings include outdoor kids activities (weather permitting), an indoor craft station, a bonfire, a fall photo booth, homemade donuts from Heavenly Bakery, spirit tastings and food specials. Free face painting and live music by The Headwaters Band are listed from noon to 2 p.m.; The Outfit String Band is listed from 3 to 6 p.m.

Tunnel of Trees Fall Drive: Tesla Owners Club of Michigan’s sixth annual Tunnel of Trees Fall Drive meets at 11 a.m. Saturday, Oct. 17, at Bière de Mac Brew Works, 14277 Mackinaw Highway in Mackinaw City, the club’s event page says. The listing describes a free, family-friendly lunch meetup, a photo stop, a 1–3 p.m. drive through Cross Village and the Tunnel of Trees, and a mixer afterward at State Road Bar & Grill, with appetizers and nonalcoholic drinks provided. The club notes a small detour on M-119 after winter flooding washed out part of the road. Confirm timing and parking with the organizers before you go.

Sources:
Petoskey Area Visitors Bureau, “The Highlands Harvest Fest,” accessed Oct. 15, 2026, https://petoskeyarea.com/events/the-highlands-harvest-fest-2/
Gypsy Distillery, “Fall Fest at Gypsy Distillery,” accessed Oct. 15, 2026, https://www.gypsydistillery.com/live-music-events/fall-fest-at-gypsy-distillery
Tesla Owners Club of Michigan, “2026 Tunnel of Trees Fall Drive,” accessed Oct. 15, 2026, https://www.teslamichigan.org/events-1/2026-tunnel-of-trees-fall-drive
Photo: Dwight Burdette, “Pumpkin Patch, Pillera Farm, Superior Township (Ypsilanti), Michigan - panoramio.jpg,” Oct. 23, 2012, Wikimedia Commons, CC BY 3.0 (https://creativecommons.org/licenses/by/3.0/), cropped and color-adjusted, https://commons.wikimedia.org/wiki/File:Pumpkin_Patch,_Pillera_Farm,_Superior_Township_(Ypsilanti),_Michigan_-_panoramio.jpg

The Straits

Tags: The Straits · Michigan Travel · Harbor Springs · Petoskey · Harvest Fest · Fall Fest