Things to do in the Inland Empire — October 2019


There’s plenty of things to do in the Inland Empire — events, family activities and fun weekend happenings! Here are some great options for the month of October — with things to do in Redlands, Yucaipa and throughout the Inland Empire!

Inland Empire events and things to do

Oct 2 | Coffee with a Cop

Join your neighbors and members of the Redlands Police Department for coffee and open conversation regarding your community. No agenda or speeches, just a chance to ask questions, voice your concerns and get to know the Redlands Police Department officers in YOUR neighborhood.

When: Wednesday, Oct 2 | 5 – 7pm
Where: Starbucks | 627 Orange St, Suite D, Redlands, California 92374
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Oct 5 | Redlands Oktoberfest 2019

9th Annual Redlands Optimist Club Oktoberfest at Sylvan Park in Redlands California. This is a kid-friendly event, with a play area containing various games and a bounce house. There is plenty of fun available for the adults as well, with contests for best costume, Yodeling, Stein Holding, and Hammerschlagen. A live German band will perform your favorite polkas, multiple vendors will have authentic German food to whet the appetite and of course, beer!

When: Saturday, Oct. 5 | 12pm – 7pm
Where: Sylvan Park | 601 N University Street, Redlands, California 92374
Cost: $10 | 20yr and under free
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Oct 5 | 2019 Redlands Conservancy Fall Social – Twilight at the Asistencia

Join Redlands Conservancy for a gala evening at the beautiful Asistencia. This historical landmark was constructed in 1930 over the San Gabriel Mission Outpost foundation. Twilight in the courtyard will recall early days in California, with a seated dinner, signature cocktail and live music. Bid on the live and silent auctions, or take a chance with opportunity baskets.

When: Saturday, Oct 5 | 5:30-10pm
Where: The Asistencia | 26930 Barton Road, Redlands, CA 92373
Cost: $120-250
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Oct 5 | Fall Fest at San Timoteo Canyon Schoolhouse

This free family event explores the 1883 San Timoteo Canyon Schoolhouse, a beautiful historic gem just west of Beaumont on San Timoteo Canyon Road. The celebration features a flag-raising at 10 a.m., a barbershop quartet, vintage games and May pole, light fare at old-fashioned prices provided by Beaumont Kiwanis Club, a Model A and 1931 fire engine, self-guided tours, Mark Twain and costumed history interpreters, and a local history exhibit.

When: Saturday, Oct 5 | 10am – 2pm
Where: San Timoteo Canyon Schoolhouse | 31985 San Timoteo Canyon Rd, Redlands, CA 92373
Cost: Free
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Oct. 11 & 12 | Autumnfest

The Autumnfest takes place in Historic Uptown in Yucaipa, CA.

When: Friday, Oct 11, 6 – 10pm | Saturday, Oct 12, 3 – 9pm
Where: Uptown Yucaipa, CA
Cost: Free
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Oct 27 | Downtown Redlands Art Walk

The DTR artwalk is a biannual event pairing local business with local artists.

When: Oct. 27 | 12pm – 5pm
Where: Downtown Redlands
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October | Apple Season in Oak Glen

Fall means that it’s apple season in Oak Glen. Shops, apple orchards, activities, events, and so much happens up in Oak Glen during apple season.

Where: Oak Glen
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Every Thursday | Redlands Market Night

Established in 1988, Redlands Market Night has established itself as one of the most successful certified farmers markets in Southern California! Vendors vie to participate in the event that has attracted thousands of weekly visitors since its inception. Visitors are welcomed into an inviting atmosphere complete with lighted trees, brick sidewalks, historic buildings, and great musical entertainment. Crowds are pleasantly surrounded by over 150 food and merchandise booths, not to mention the downtown shopkeepers, every Thursday night.

When: Ongoing Thursday nights, 6 – 9pm
Where: 1 East State Street, Redlands, CA 92373
Cost: Free entrance
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