🎃 2026 HALLOWEEN GUIDE • UPDATED OCT 28
Halloween Events & Trunk-or-Treats in Midlothian, Moseley & Chesterfield, VA
Every family-friendly and grown-up Halloween plan we confirmed for Thursday, Oct 29 through Sunday, Nov 1, 2026 across Midlothian, Moseley and Bon Air (23112, 23113, 23114, 23120 and 23235). We checked each time, address and price against the organizer’s own page. Plans can change, so tap through before you head out.
🖍️ Free Download: The 2026 Midlothian Halloween Kids Activity & Coloring Pack
Five printable 8.5×11 Halloween PDF coloring sheets (plus our new Thanksgiving & Christmas packs—11 local sheets total!). Enter your email to unlock instant PDF downloads, or browse all 11 sheets on the coloring page →
🎃 Family & Kids Trick-or-Treating
- Trunk or Treat at Tomahawk Baptist Church — Sat, Oct 31, 5:00–7:00 PM
Tomahawk Baptist Church, 12920 Hull Street Rd., Midlothian, VA • Free
Free all-ages costume night with decorated trunks and candy. Details → - Halloween in the Village — Sat, Oct 31, 4:00–7:30 PM
Powhatan Courthouse Village, Powhatan, VA
Village trick-or-treating just west of Midlothian. Details → - The Glow Up Sneaker Ball — Fri, Oct 30, 5:30–8:00 PM
Beulah Recreation Center, 6901 Hopkins Rd., N. Chesterfield, VA • Free (register at Chesterfield.gov/Parks, course 50612)
Free Chesterfield Parks & Rec family night with music, games and food, DJ Amare. Wear your favorite sneakers. Details → - Pre-K Story Time (ages 3–5) — Fri, Oct 30, 10:00–10:30 AM
Midlothian Library (Activity Room), Midlothian, VA • Free (registration required)
Stories, songs and creative play. Register each child. Details →
🧺 Daytime Workshops & Markets
- Kids’ Trick-or-Treat Basket Workshop — Sat, Oct 31, 10:00–11:00 AM
Cross Creek Nursery (Midlothian), 501 Courthouse Rd., Richmond, VA • $15 per craft (registration required)
Kids decorate a trick-or-treat basket with stickers and ribbon. Details → - Latino Farmers Market on Hull Street — Sat, Oct 31, 8:00 AM–1:00 PM
Chesterfield Technical Center, 13900 Hull Street Rd., Midlothian, VA
Empanadas, tamales, local produce and face painting for kids. Details →
🎸 Live Music & Adult Halloween Nights
- 2nd Annual Thriller Night (21+) — Sat, Oct 31, Doors 8:00 PM, music 9:00 PM
Uptown Alley, 6101 Brad McNeer Pkwy., Midlothian, VA • Ticketed; lanes sold separately
Grown-up Halloween party headlined by Andrew Hypes. Details → - Halloween Costume Party with Southern Hash Society — Sat, Oct 31, 6:00–9:00 PM
Crazy Rooster Brewing (The Coop), 1560 Oakbridge Dr., Powhatan, VA
Live music and costumes, with ROJO’S Smoke Shack on site. Details → - Boos & Brews Live Rock Kickoff with TEAZE — Fri, Oct 30, Music 9:00 PM
Uptown Alley, 6101 Brad McNeer Pkwy., Midlothian, VA
Halloween-weekend rock kickoff. Details → - Trivia with Big Brainz Live! — Fri, Oct 30, 6:30–8:30 PM
Waters Edge Winery, 2201 Chartermark Dr., Midlothian, VA
Halloween-eve wine and trivia. Details → - Burger Night & Taproom Trivia — Thu, Oct 29, Burgers 4–9 PM, trivia 6:30–8:30 PM
Hidden Wit Brewing, 21110 Hull Street Rd., Moseley, VA
Burger night and weekly trivia in Moseley. Details → - Pat O’Brien Live at Waters Edge Winery — Sun, Nov 1, 2:00–4:30 PM
Waters Edge Winery, 2201 Chartermark Dr., Midlothian, VA • Reservations recommended
Laid-back Sunday afternoon set. Details →
🚗 Worth the 15-Minute Drive
- Maymont Garden Glow — Thu, Oct 29 & Sat, Oct 31, Thu, Oct 29 is Latin Night and Sat, Oct 31 is Adults-Only Night (open select nights through Sun, Nov 8)
Maymont, Richmond, VA • Adult tickets $20 (value nights)–$25; buy in advance
Light displays, fire pits and food trucks, about 15 minutes away. Details →
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