9 October-ish things to do for Halloween in Sherwood
Where will you haunt on the spookiest nights of the year?
SHERWOOD, Ore. — Keep the holiday spirit haunting all month with these local, family-friendly Halloween parties from our calendar just for you — whether you're looking for trunk-or-treating, costume contests, harvest festivals, or just wine. We’ve found candy, drinks, music, photo opps, costume contests, and more to help you celebrate the 'ber months.
Remember to always add your events to the Sherwood Sun Calendar — it’s free advertising that supports your event and gets the word out to your target market right here in town!
Red Berry Barn, 19200 S.W. Chapman Rd.
Sept. 19-Oct. 31, 9 a.m.-6 p.m.
Admission: $15-25
Kids, adults, and seniors are welcome at the Red Berry Barn's Fall Harvest Festival to enjoy fall activities including picking pumpkins, bakes goods, fall decor shopping, photo opps, and outdoor games like a giant bounce pumpkin, mega slide, zip lines, obstacle courses, corn barn, hay slide, and farm animals.
Southwest Pinehurst Drive
Oct. 2-31 weekends, 7-8 p.m.
Admission: Free
All along Pinehurst Court, families can view extreme Halloween decorations featuring animatronics, lights, fog, and a ten-minute show.
It's free to come out and see the displays, the show, and trick-or-treat, with sponsors helping to raise money for the Sherwood Education Foundation.
On Halloween night, trick-or-treaters can return gold in exchange for candy. The gold can be found along Sherwood’s public trails.
Jules Rogers
Sherwood Heritage Center, 2252 Park St.
Oct. 3-24 Saturdays, 7 p.m.
Admission: $5-10
Families can book reservations at Haunted Sherwood, and immerse themselves in local ghost stories from the past at the Sherwood Heritage Center.
Jules Rogers
4. The Haunting 2026: Welcome to the Halloween Society
Sherwood Center for the Arts, 22689 S.W. Pine St.
Oct. 8-10, 7 p.m.
Admission: $20
This family-friendly live performance showcase raises funds for youth pursuing their love of the arts, and is hosted by the Passages Arts Connection and the Collective Dance Company.
Our Table Cooperative, 13390 S.W. Morgan Rd.
Oct. 17, 5:30 p.m.
Admission: $150
Celebrate Diwali, the festival of lights, with a fabulous home-cooked Indian meal prepared by Narendra Varma, founder of Our Table, with wine pairings from local wineries. This event is for those 21 and older.
6. 6th Annual Pinots and Pumpkins Fall Harvest Party
Olea Vineyards, 17406 S.W. Parrett Mountain Rd.
Oct. 24, Noon-5 p.m.
Admission: $33.85
Join in an afternoon of food, fun, friends, and most importantly, wine! Celebrate the 2026 harvest and 10 years of Olea Vineyards with old favorites and newly released bottles, accompanies by small bites.
7. Trunk-or-Treat at Cars and Coffee
Langer's Entertainment Center parking lot, 21650 S.W. Langer Farms Pkwy.
Oct. 31, 8-11 a.m.
Admission: Free
Kids, teens, and adults are welcome to join Cars and Coffee for a Trunk-or-Treat special, including a costume contest at 9 a.m. with awards, candy, and photo opportunities.
8. Trick-or-Treat in Old Town Sherwood
Robin Hood Festival Plaza, S.W. 1st and Pine Streets
October 31, 3-6 p.m.
Admission: Free
Old Town streets will close while participating Old Town businesses will hand out candy to trick-or-treaters, and the Robin Hood Festival Plaza will have even more organizations joining in. This event is family-friendly.
9. Potluck and Halloween Costume Party
Sherwood American Legion Post 56
October 31, 7 p.m.
Admission: A dish to share
An annual potluck-style dinner, festival decorations, and a costume contest with special prizes is slated for the Sherwood American Legion Post 56.
