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
Hoosier Fall Festival
October 17 - 18, 2026
hoosierfallfestival.com
(317) 556-5326
Johnson County Fairgrounds - Franklin, IN
We will be offering a wide range of items from local artisans. Crafts, t-shirts, florals, farmhouse decor, jewelry, photography, painted items, clothing, baked goods, jewelry, soaps, holiday decor and so much more. We will have food trucks ranging from tacos and barbecues to deserts and kettle corn. You can purchase your seasonal pumpkins and mums along with other wonderful fall merchandise. The atmosphere will abound with fall vibes and you can take your picture at one of our photo ops. Music, face painting, roaming characters, and balloons will also add to the festivities. Come join us on Saturday and Sunday, Oct.17 & 18.
Events in Portland, IN — upcoming
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 26 - 29, 2026
Antique Engine & Tractor Show
Jay County Fairgrounds, Portland, IN
Status: Updated 3/12/2026
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.
March 2027 (dates not updated)
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.
