Wawasee Fine Arts Festival at Oakwood
May 23, 2026
chautauquawawasee.org
(574) 377-7543
Oakwood Resort - Syracuse, IN
The outdoor setting provides a family-friendly environment. Food vendors are onsite for snacks and lunch, with outside seating available. Also, the Pier and Back Porch at Oakwood offers a full menu with both indoor and outdoor lakefront dining overlooking beautiful Lake Wawasee. Children's activities and playgrounds are available. Attendance is free. Stop by the Chautauqua booth for a giveaway.
Strawberry Festival
June 12 - 14, 2026
crawfordsvillestrawberryfest.com
(765) 918-2759
Lane Place Antebellum Mansion - Crawfordsville, IN
Three days of food, crafts, children's booths, athletic events, car shows and fantastic entertainment with Friday and Saturday nights of national-level entertainment shows.
Madison Chautauqua Festival of Art
September 26 - 27, 2026
madisonchautauqua.com
(800) 559-2956
Historic Neighborhood - Madison, IN
Southern Indiana's premier fine arts & crafts festival. Handmade work by exhibitors from across the United States. Activities include entertainment, a food fest, a beer/wine garden, a chalk walk, and kids area.
Bloomfield Apple Festival
October 2 - 4, 2026
bloomfieldapplefestival.org
(614) 600-4218
Town Park - Bloomfield, IN
Come experience autumn magic at one of Southern Indiana's most beloved fall festivals, known for its warm small-town charm and fun-filled variety Enjoy: 🎡Carnival rides, games, and friendly contests, including tractor pulls and wiffle ball tournaments 🍎Tasty bites and local flavors at food booths 🎶 Live music, a parade, and stage performances running all weekend long
Events in Portland, IN — upcoming
March 6 - 7, 2026
Jay County Fiber Arts Festival
Jay County Fairgrounds, Portland, IN
Status: Updated 1/20/2026
This Indiana Fiber Arts Festival will have crafts and fine craft exhibitors, and 1 food booth.
May 2026 (dates not updated)
Tri-State Swap & Sell Meet - Spring
Tri-State Club Grounds, Portland, IN
Status: Updated 3/21/2025
This Indiana Antiques Collectibles Show will have antique/collectibles exhibitors and no food booths. Admission tickets are $5. This event will also include consignment auction on saturday at 1:00 pm.
May 2026 (dates not updated)
Spring Kroozen the Courthouse
Downtown Portland, Portland, IN
Status: Updated 3/28/2025
This Indiana Boat Auto Camping Show will have no exhibit booths and tba food booths. There will be 1 stage with Local talent and the hours will be Sat 1pm-7pm. This event will also include live music.
August 2026 (dates not updated)
Antique Engine & Tractor Show
Jay County Fairgrounds, Portland, IN
Status: Updated 3/12/2025
This Indiana Antiques Collectibles Show will have antique/collectibles and crafts exhibitors, and no food booths. There will be 1 stage with Regional and Local talent and the hours will be . Admission tickets are $5.
September 2026 (dates not updated)
Jay County Heritage Festival
Jay County Historical Museum Grounds, Portland, IN
Status: Updated 9/16/2025
This Indiana Festival will have antique/collectibles, crafts, film, fine art, fine craft and homegrown products exhibitors, and tba food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 11am-6pm; Sun 11am-4pm. This event will also include: storytellers, quilters, wood carving, candle dipping, cider press operations.
October 2026 (dates not updated)
Tri-State Fall Swap & Sell Meet
Tri-State Grounds, Portland, IN
Status: Updated 3/21/2025
This Indiana Antiques Collectibles Show will have antique/collectibles and flea market exhibitors, and no food booths. Admission tickets are $5. This event will also include none.
November 2026 (dates not updated)
Delts' Craft Show
Jay County High School, Portland, IN
Status: Updated 11/2/2025
This Indiana Craft Show will have crafts, fine art and fine craft exhibitors, and local food booths. Admission tickets are $2.
