12 Best Southern Oregon Events to Attend in August 2026
By The Rockwell Group | Updated August 5, 2026
Looking for the best things to do in Southern Oregon in August 2026? This month’s calendar is packed with outdoor concerts, professional theater, motorsports, wine events, family activities, live comedy, baseball, and one-of-a-kind Rogue Valley experiences.
Some events appear several times on the original calendar because they include multiple performances, tournament days, or recurring dates. To keep this guide useful and avoid repetition, each festival, series, production, or tournament is included as one main event. For example, the Oregon Shakespeare Festival, Flynn Creek Circus, American Legion Northwest Regional, and Medford Rogue Rotary Pickleball Fest each span multiple days but are treated as individual experiences.
Here are 12 of the most unique Southern Oregon events to add to your August plans.
1. Oregon Shakespeare Festival 2026 Season
Event title: Oregon Shakespeare Festival 2026 Season
Date and time: Throughout August 2026; matinee and evening performance times vary
Location: Oregon Shakespeare Festival, 15 S. Pioneer Street, Ashland, Oregon
The Oregon Shakespeare Festival is one of the defining cultural experiences in Southern Oregon. Rather than being one standalone performance, OSF presents a rotating schedule of plays in multiple theaters throughout its Ashland campus.
August productions include A Midsummer Night’s Dream, Come From Away, Emma, Henry IV, Part One, August Wilson’s King Hedley II, The Taming of the Shrew, Yellow Face, You Are Cordially Invited to the End of the World! and Smote This, A Comedy About God… and Other Serious $HT*.
Because each production appears repeatedly throughout the calendar, OSF is included here as one main festival experience. Visitors can choose a single show or build an entire theater weekend around multiple productions.
2. American Legion Baseball Northwest Regional Tournament
Event title: American Legion Baseball Northwest Regional Tournament
Date and time: August 5–9, 2026; game times vary by day and bracket
Location: Harry & David Field, 2929 S. Pacific Highway, Medford, Oregon
Five days of tournament baseball are coming to Harry & David Field as eight teams compete in the American Legion Region 7 Northwest Regional.
The field represents seven Western states, with an additional spot for the host team. The tournament follows a double-elimination format, and the regional champion advances to the American Legion World Series in Shelby, North Carolina.
This is one multi-day tournament, even though it is listed separately on each day from August 5 through August 9. Baseball fans can attend a single game, purchase a tournament pass, or follow the bracket as teams advance toward the championship round.
3. Mt. Ashland Drive-In Movie Night Series
Event title: Mt. Ashland Drive-In Movie Night
Date and time: August 8, 15 and 22, 2026; parking opens at 7 p.m. and movies begin at 9 p.m.
Location: Mt. Ashland Ski Area, 11 Mt. Ashland Ski Road, Ashland, Oregon
Trade the traditional movie theater for a mountaintop screening under the stars. Mt. Ashland’s Drive-In Movie Night series invites visitors to bring blankets, chairs, or a comfortable truck-bed setup and watch a classic film in the ski-area parking lot.
The remaining August lineup includes:
- August 8: Mary Poppins
- August 15: Night of the Living Dead
- August 22: The Goonies
Concessions open at 8 p.m., and sound is transmitted through vehicle radios. The August 22 screening is currently marked sold out, so moviegoers should check the official event page for the latest availability before traveling to the mountain.
4. Rogue Valley Comic Book Expo
Event title: Rogue Valley Comic Book Expo
Date and time: August 8, 2026, from 10 a.m. to 5 p.m.
Location: Phoenix Plaza Civic Center, 220 N. Main Street, Phoenix, Oregon
Comic collectors and pop-culture fans can spend the day browsing thousands of comics and meeting the artists, writers, and sellers behind them at the Rogue Valley Comic Book Expo.
The event is intentionally focused on comic books rather than functioning as a broad entertainment convention. Guests can search seller boxes for missing issues, discover local creators, and connect with other collectors.
General admission is $5, while children 12 and younger receive free admission. The event appears only once on the August calendar and is a standalone expo.
5. Concert at the Rocks
Event title: Concert at the Rocks
Date and time: August 8 and August 22, 2026; departure times vary by ticket block
Location: Jet-boat departure from Touvelle State Park, 8601 Table Rock Road, Central Point; concert held at Discovery Park
Concert at the Rocks combines live music, a jet-boat ride, Rogue River scenery, and an outdoor venue beneath the Table Rock cliffs.
The August performers are:
- August 8: The Brothers Reed
- August 22: Evening Shades
Standard tickets include round-trip jet-boat transportation from Touvelle State Park to Discovery Park. Guests choose from designated departure blocks, with the complete experience lasting approximately four hours and including around two hours of live music.
Because both dates are part of the same summer concert series, they are grouped as one main event rather than two unrelated concerts.
6. ZZ Top and Cheap Trick
Event title: ZZ Top and Cheap Trick
Date and time: August 13, 2026, at 7 p.m.
Location: Bi-Mart Amphitheater at the Jackson County Expo, Central Point, Oregon
Two legendary rock bands take the stage together when ZZ Top and Cheap Trick arrive at the Jackson County Expo.
This is expected to be one of Southern Oregon’s largest concerts of the month, bringing decades of recognizable rock music to the Bi-Mart Amphitheater for one night.
Although two performers are named, this is one ticketed concert with Cheap Trick joining ZZ Top on the same bill. Ticket prices and seating availability may change as the event approaches.
7. Legends of Dirt Modified Shootout
Event title: Legends of Dirt Modified Shootout
Date and time: August 13–15, 2026; test and tune runs August 13 from 6–10 p.m., with racing August 14–15
Location: Southern Oregon Speedway, 6900 Kershaw Road, White City, Oregon
The second annual Legends of Dirt Modified Shootout brings three days of high-energy motorsports to Southern Oregon Speedway.
The weekend begins with a test-and-tune session on Thursday. Modified qualifying and heat races follow on Friday, leading into Saturday’s consolation races, Top 10 Challenge, and main event.
The finale offers $10,000 to win and $1,000 to start, making it one of the region’s most significant dirt-track racing events of the year. The separate calendar listings on August 13, 14 and 15 all belong to the same race weekend.
8. Flynn Creek Circus Presents The Cricket & the Wren
Event title: Flynn Creek Circus Presents The Cricket & the Wren
Date and time: August 14–23, 2026; performances begin between 1 p.m. and 8 p.m., depending on the date
Location: Under the Big Top at ScienceWorks Hands-On Museum, 1500 E. Main Street, Ashland, Oregon
Flynn Creek Circus returns to Ashland with The Cricket & the Wren, an original all-human fairytale told through acrobatics, storytelling, juggling, comedy, aerial performance, and athletic skill.
The story follows a merchant’s daughter on a journey to break the Frog Prince’s spell. The theatrical format makes it more than a traditional circus, combining a complete narrative with high-flying performances.
There are multiple family-friendly matinees and evening shows throughout the run. Select 8 p.m. performances are designated for adults 21 and older, so guests should review the individual showtime before purchasing tickets.
All calendar listings from August 14 through August 23 represent performances of the same production.
9. Indie Wine Mixer: Southern Oregon Edition
Event title: Indie Wine Mixer: Southern Oregon Edition
Date and time: August 15, 2026, from noon to 5 p.m.
Location: Phoenix Plaza Civic Center, 220 N. Main Street, Phoenix, Oregon
The Indie Wine Mixer celebrates the small producers and winemaker-owned labels helping shape Oregon’s wine industry.
More than 20 independent Oregon winemakers are expected to gather at the Phoenix Plaza Civic Center. Attendees can meet the people who make the wines, sample small-production releases, and purchase bottles directly from participating producers.
Food trucks, DJs, and a community-focused atmosphere help distinguish the mixer from a traditional formal wine tasting. This is a standalone event and should not be grouped with the calendar’s many individual winery music performances.
10. Medford Rogue Rotary Pickleball Fest
Event title: Medford Rogue Rotary Pickleball Fest presented by Lithia 4 Kids
Date and time: August 28–30, 2026; daily match times are assigned by tournament organizers
Location: The Courts by Lithia & Driveway at Wes Howard Memorial Sports Park, 1221 N. Ross Lane, Medford, Oregon
Pickleball players take over Medford’s new 19-court facility for the sixth annual Rogue Rotary Pickleball Fest.
The three-day schedule includes:
- August 28: Women’s doubles and men’s singles
- August 29: Mixed doubles and youth events
- August 30: Men’s doubles and women’s singles
Competition follows a round-robin format with medal playoffs. Skill divisions range from 3.0 through 4.5 and above, with age brackets determined after registration closes.
The tournament registration page identifies the larger location as Howard Memorial Sports Park, while the dedicated courts are officially known as The Courts by Lithia & Driveway. The August 28, 29 and 30 listings all represent the same tournament.
11. Oregon Honey & Mead Festival
Event title: Oregon Honey & Mead Festival
Date and time: August 29, 2026, from noon to 5:30 p.m.
Location: EdenVale Winery, 2310 Voorhies Road, Medford, Oregon
The Oregon Honey & Mead Festival offers a sweet combination of local flavor, live entertainment, vendors, and environmental education.
Guests can explore honey and mead, learn tasting techniques from experts, meet beekeepers, and hear from speakers who specialize in pollinators and pollination. The entertainment lineup includes the Danielle Kelly Soul Project and bluegrass music from Mountaintop Sound.
The festival also includes pollinator-gardening advice and educational presentations. Children are admitted free with a parent, and the venue describes the festival as family-friendly with space for kids.
Proceeds support Cascade Girl Organization and its educational work involving pollinators, agriculture, veterans, children, and the local community.
12. The Trouble with Angels Starring Jane Lynch and Kate Flannery
Event title: The Trouble with Angels starring Jane Lynch and Kate Flannery
Date and time: August 29, 2026, at 7 p.m.
Location: Craterian Theater at the Collier Center, 23 S. Central Avenue, Medford, Oregon
Jane Lynch and Kate Flannery bring comedy, music, vocals, classic tunes, and cabaret-style banter to the Craterian Theater for a one-night performance of The Trouble with Angels.
The live show gives audiences an opportunity to see the two television performers step beyond their familiar screen roles for an evening built around their friendship, comic timing, music, and playful stage chemistry.
The event is listed twice on the original August calendar, but both listings refer to the same August 29 performance.
Frequently Asked Questions About Southern Oregon Events in August 2026
What are the best events in Southern Oregon in August 2026?
Some of the month’s standout events include the Oregon Shakespeare Festival, American Legion Baseball Northwest Regional, Concert at the Rocks, ZZ Top and Cheap Trick, Flynn Creek Circus, the Indie Wine Mixer, Oregon Honey & Mead Festival, and The Trouble with Angels.
Which August events are good for families?
Family-friendly possibilities include the Rogue Valley Comic Book Expo, American Legion Baseball, selected Flynn Creek Circus performances, the Oregon Honey & Mead Festival, and the Mary Poppins screening at Mt. Ashland. Families should check individual age guidance because Night of the Living Dead is rated R and certain Flynn Creek Circus evening performances are restricted to guests 21 and older.
Why are some calendar events grouped together?
Some listings are individual dates within a larger production, tournament, or series. The Oregon Shakespeare Festival, Drive-In Movie Nights, Concert at the Rocks, Flynn Creek Circus, baseball regionals, Legends of Dirt, and the pickleball tournament are therefore presented as seven main experiences rather than dozens of repetitive calendar entries.
Where are most August events happening?
Most of the featured events are located in Medford, Ashland, Central Point, Phoenix, and White City, making it possible to explore several Rogue Valley communities throughout the month.
Experience More of Southern Oregon With The Rockwell Group
Southern Oregon’s theater, wineries, outdoor recreation, live music, sporting events, and welcoming communities are just a few reasons people choose to call the Rogue Valley home.
Whether you are searching for your first home, planning a move within Southern Oregon, selling a property, or exploring real estate investment opportunities, The Rockwell Group is ready to help you understand the market and move forward with confidence.
Explore Southern Oregon homes and connect with The Rockwell Group, or call 541-292-4444 to speak with the team.
Disclaimer: Event dates, times, locations, schedules, age restrictions, ticket prices, and availability are subject to change. Information was researched and verified as of August 5, 2026. The Rockwell Group is not affiliated with, responsible for, or an organizer of the events included in this article. Readers should confirm current information directly with each event organizer or venue before purchasing tickets or attending.
