10/23-25 - Churchill & Roosevelt: The Christmas That Saved The World at The Delray Beach Playhouse, 950 NW 9th St. F/Sat: 7:30 pm; Sat/Sun: 2 pm. $69. 561-272-1281; delraybeachplayhouse.com
10/24-25 - 26th Annual Orchids on the Square: Delray Beach Orchid Society Annual Show and Sale at Vintage Gym at Old School Square, 51 N Swinton Ave. Sat 10 am-5 pm; Sun 10 am-4 pm. $5/admission; free/child under 6. 561-573-7633; delraybeachorchidsoc
10/24 - Annual Halloween Parade & Kidsfest starts at SE/NE 5th Ave, ends at Old School Square Amphitheater, 51 N Swinton Ave, Delray Beach. Family fare. Trick-or-treating: 11:30 am-1 pm; Kidsfest: 11 am-3 pm; parade: 1 pm. Free. 561-243-1077; delrayo
10/24 - Pumpkin Palooza at The Shops at Boca Center, 5150 Town Center Circle. All proceeds from pumpkin sales will benefit Cason United Methodist Church. 2-5 pm. bocacenter.com
10/24 - 2026 Boca Raton Mayors Ball at The Boca Raton, 500 E Camino Real. Presented by The Rotary Club Downtown Boca Raton. Reception, dinner, dancing, awards presentation. 6:30 pm. $595. 561-299-1429; rotarydowntownbocaraton.org/mayors-ball/
10/25 - Lights, Camera, Music! at First Presbyterian Church of Delray Beach Courtyard, 33 Gleason St. Part of the First Delray Concert Series. 4 pm. $20. 561-276-6338; firstdelray.com
10/27 - 2nd Annual Shakesfear! at Delray Beach Historical Society, 1926 Historic Bungalow, 3 NE 1st St. Featuring presentation of William Shakespeare’s readings by the Shakespeare Troupe of South Florida. All ages. 6 pm. $15/person; free/members. Reg
10/28 - Little Boo Halloween Parade at Boynton Beach Library, 100 E Ocean Ave. Ages 0-5. 10-11:30 am. Free. Registration: 561-742-6390; boyntonlibrary.org
10/28 - Sole Mates Luncheon 2026 at Boca West Country Club, 20582 Boca W Dr, Boca Raton. Benefits Best Foot Forward Foundation. 11:30 am-1:30 pm. $125/person. 561-470-8300; bffsolematesluncheon.com
10/29 - Boo Bash - A Halloween Dance! at Boynton Beach Library, 100 E Ocean Ave. Ages 5-11. 5-6:30 pm. Free. Registration: 561-742-6390; boyntonlibrary.org
10/30 - Annual Halloween Fall Fest at Delray Beach Historical Society, 3 NE 1st St. Featuring outdoor movie, costume contest, crafts, raffles, history exhibits, storyhour and more. 5-9 pm. $25/person; free/ages 12 & under. Registration: 561-274-9578;
10/30 - Estate Planning Seminar at Boynton Beach Library, 100 E Ocean Ave. Adults. 5:30-6:30 pm. Free. Registration: 561-742-6390; boyntonlibrary.org
10/30 - Little Scream! at Bryant Park, 100 S Golfview Rd, Lake Worth Beach. Costume contest, trunk-or-treat fun, games & activities. 6-9 pm. 561-586-1600; lakeworthbeachfl.gov
10/30 - Scream on the Green at Wilson Park, 225 NW 12th Ave, Boynton Beach. Family-friendly spooky movie on the lawn. 7 pm. Free. 561-742-6000; boynton-beach.org
10/30-31 - Dracula - A Live Radio Play at Lake Worth Playhouse, 713 Lake Ave. Part of the Live Radio Play Series. F: 7:30 pm; Sat: 2 pm. $25. 561-586-6410; lakeworthplayhouse.org
10/31 - Boo Bash! at Delray Beach Library, 100 W Atlantic Ave. All ages. 11 am-noon. Free. Registration: 561-266-0194; delraylibrary.org
10/31 - Halloween Pumpkin Painting at Delray Beach Library, 100 W Atlantic Ave. Ages 13-17. 11 am-12:30 pm. Free. Registration: 561-266-0194; delraylibrary.org
11/1 - Sugar Plum Fairy Tea at The Studio at Mizner Park, 201 W Plaza Real, Boca Raton. Features cast of characters from The Nutcracker, specialty teas, mimosas, lemonade and small bites plus a silent auction. All proceeds benefit Boca Ballet Theatre
11/4 - Coral Reef Conservation and Restoration at Delray Beach Library, 100 W Atlantic Ave. Part of the Ocean Science Lecture Series with Pinnacle Ecological. 2-3:30 pm. Free. Registration: 561-266-0194; delraylibrary.org
11/7-8 - Art on the Square Fine Art Show at Old School Square Amphitheatre, 51 N Swinton Ave, Delray Beach. Sat: 10 am-5 pm; Sun: 10 am-4 pm. Free. 561-243-1077; delrayoldschoolsquare.com
