Events calendar
City festivals, holiday parades, state park nights, markets and the nearby squares, in one place for anyone living in or looking at Middleton. Every listing links to the page it was checked against, with the date it was checked.
Updated October 16, 2026 · 26 upcoming events · Refreshed weekly by Cristian Gonzalez, REALTOR®, eXp Realty
As of October 16, 2026, this calendar lists 26 upcoming events in and around Middleton and Wildwood through December 19, 2026; 8 are free. City festivals, holiday parades, state park events, markets and nearby square nights are all here. Every listing links to its source and the date it was checked.
Middleton is a separate community from The Villages. Events listed in The Villages are the public town square events, labeled as such.
Also weighing The Villages? Events in and around The Villages has the full town square calendar.
Friday, October 16, 2026
Check-in 4:00 p.m., dinner 4:30 p.m., show 5:00 p.m. · $35 · Registration required
Historic Baker House, 6106 CR 44A, Wildwood FL
Dinner theater at the historic Baker House where guests help solve a murder from the past. Final date of the fall run. Advance registration required; no alcohol or smoking.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
October 16, 2026 to November 30, 2026
Sun to Thu 5 to 9 p.m.; Fri and Sat 6 to 10 p.m. · Varies · Open to the public
Sawgrass Grove and Brownwood Paddock Square, The Villages
Nightly live music at the two Villages town squares closest to Middleton. Located in The Villages, not Middleton. Cost not listed on the calendar.
Source: The Villages, Seasons of Celebration calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
October 16, 2026 to November 1, 2026
Free · Open to the public
Wildwood Police Department, 8942 N. US-301, Wildwood FL
Community donation drive collecting hygiene items. Drop-offs at Wildwood PD or the Fifth Third Bank on Burnsed Blvd. Call 352-931-0357 to sponsor baskets.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 17, 2026
10:00 a.m. to 11:00 p.m.; parade at 10:00 a.m., fireworks after dark · Varies · Open to the public
Marge A. Thies Plaza Park, 117 E. Joe P. Strickland Jr. Ave, Bushnell FL
Bushnell's long-running fall festival opens with a morning parade, then a full day of games, contests, food, crafts, music and dance, closing with fireworks after nightfall.
Source: City of Bushnell; Discover Sumter event listing, checked October 16, 2026. Google Calendar · Apple or Outlook
Sunday, October 18, 2026
1:30 to 5:00 p.m. · $75 to $100 · Registration required
Wildwood Vineyard and Events, 1945 E CR 462, Wildwood FL
A seven-course meal paired with a movie screening at a Wildwood vineyard venue. Reservations are taken in advance through the venue.
Source: Discover Sumter, checked October 16, 2026. Google Calendar · Apple or Outlook
October 19, 2026 to December 28, 2026
Mondays 7:00 a.m. to 2:00 p.m. (winter hours) · Free · Open to the public
Webster Westside Flea Market, 516 NW 3rd Street, Webster FL
Weekly Monday flea market in Webster, open every week rain or shine. Gates open to vendors at 6 a.m. No visitor admission fee listed.
Source: Webster Westside Flea Market, checked October 16, 2026. Google Calendar · Apple or Outlook
October 20, 2026 to December 29, 2026
Tuesdays 10:30 a.m. · $20 · Registration required
Historic Baker House, 6106 CR 44A, Wildwood FL
Private guided tours of the restored historic Baker House for groups of 10 or more. Book by calling 352-461-0134.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Thursday, October 22, 2026
4:45 p.m. · Varies · Open to the public
Sawgrass Grove, The Villages
A Halloween zombie dance performance on the Sawgrass Grove town square, the closest Villages square to Middleton. Located in The Villages. Cost not listed.
Source: The Villages, Seasons of Celebration calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
October 23, 2026 to October 24, 2026
3:30 to 8:00 p.m. · Varies · Open to the public
Wildwood Vineyard and Events, 1945 E CR 462, Wildwood FL
Two-day Halloween gathering at a Wildwood vineyard event venue. Cost not listed on the calendar; check with the venue before going.
Source: Discover Sumter events calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, October 23, 2026
6:00 to 9:00 p.m. · $5 · Open to the public
Dade Battlefield Historic State Park, 7200 Battlefield Parkway, Bushnell FL
Annual Halloween night at the state park with a haunted trail, haunted house, food trucks and a gentler kiddie trail. $5 covers park entry; ages 5 and under free.
Source: Florida State Parks, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, October 23, 2026
6:00 to 9:00 p.m. · Free · Open to the public
Wildwood Community Center, 6500 Powell Rd, Wildwood FL
Wildwood's free Halloween party with trunk-or-treat, costume contests, hayrides, music, food trucks and candy. All ages welcome per the city.
Source: City of Wildwood Community Events; Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 24, 2026
6:00 to 9:00 p.m. · $5 · Open to the public
Dade Battlefield Historic State Park, 7200 Battlefield Parkway, Bushnell FL
Second night of the park's annual haunted event: haunted trail, haunted house, food trucks and kiddie trail. $5 per person includes park entry; ages 5 and under free.
Source: Florida State Parks, checked October 16, 2026. Google Calendar · Apple or Outlook
Monday, October 26, 2026
5:45 p.m. · Varies · Open to the public
Brownwood Paddock Square, The Villages
A Halloween season flash mob dance performance on Brownwood Paddock Square. Located in The Villages, not Middleton. Cost not listed.
Source: The Villages, Seasons of Celebration calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
October 28, 2026 to October 29, 2026
4:00 p.m. and 6:00 p.m. · $20 · Registration required
Historic Baker House, 6106 CR 44A, Wildwood FL
Evening ghost-story tours of the historic Baker House focused on the women who once lived there. All ages per the city; advance registration required.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, October 30, 2026
5:30 to 9:00 p.m. · Varies · Open to the public
Downtown Middleton, Middleton
Downtown Middleton's fall community night with DJ Scooter, games, inflatables, food and drinks, a costume contest and local business booths. Cost not stated.
Source: Middleton (mymiddleton.com), checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, October 30, 2026
6:45 p.m. · Varies · Open to the public
Brownwood Paddock Square, The Villages
Halloween zombie dance performance on Brownwood Paddock Square. Located in The Villages. Cost not listed on the calendar.
Source: The Villages, Seasons of Celebration calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 31, 2026
6:00 to 10:00 p.m. · Varies · Open to the public
Brownwood Paddock Square and other town squares, The Villages
Halloween night programming across The Villages town squares, including Brownwood. Located in The Villages, not Middleton. Cost not listed.
Source: The Villages, Seasons of Celebration calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, November 11, 2026
Free · Open to the public
Wildwood City Hall, 100 N. Main St, Wildwood FL
Patriotic displays honoring local veterans at Wildwood City Hall. The submission deadline for veteran displays was October 9. Viewing time not listed.
Source: City of Wildwood Community Events; Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, November 14, 2026
7:00 a.m. to 1:00 p.m. · Free · Open to the public
Webster Westside Flea Market, 516 NW 3rd Street, Webster FL
A Saturday yard-sale edition on the Webster flea market grounds with free visitor parking. Seller spaces run $10 to $20.
Source: Webster Westside Flea Market, checked October 16, 2026. Google Calendar · Apple or Outlook
Tuesday, December 1, 2026
5:00 to 9:00 p.m. · Varies · Open to the public
Brownwood Paddock Square and other locations, The Villages
The Villages holiday lighting kickoff, held at Brownwood and other squares. Located in The Villages, not Middleton. Cost not listed.
Source: The Villages, Seasons of Celebration calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
December 1, 2026 to December 29, 2026
Tue, Thu, Sat 4, 5 and 6 p.m.; Sun 1, 2 and 3 p.m. · $15 · Registration required
Historic Baker House, 6106 CR 44A, Wildwood FL
Holiday tours of the historic Baker House, with each room decorated by a local business or civic group. Private tours $20 per person. Advance registration required.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, December 4, 2026
Winterfest 5:00 p.m.; parade 6:00 p.m.; tree lighting 7:30 p.m.; Santa 8 to 9 p.m. · Free · Open to the public
Wildwood City Hall, 100 N. Main St, Wildwood FL
Wildwood's annual Christmas parade with community floats, then a City Hall tree lighting, treats and Santa visits. Free, all ages welcome per the city.
Source: City of Wildwood Community Events; Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, December 5, 2026
5:00 to 9:00 p.m. · Varies · Open to the public
Downtown Webster, Webster
Webster's annual downtown holiday evening with a Christmas parade, a Christmas market, lights and visits with Santa. Cost not listed by the city.
Source: City of Webster, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, December 12, 2026
7:00 a.m. to 1:00 p.m. · Free · Open to the public
Webster Westside Flea Market, 516 NW 3rd Street, Webster FL
December Saturday yard-sale edition on the Webster flea market grounds, with free visitor parking. Seller spaces run $10 to $20.
Source: Webster Westside Flea Market, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, December 18, 2026
6:00 to 8:00 p.m.; sensory-friendly hour 5:00 to 6:00 p.m. · Free · Open to the public
Wildwood Community Center, 6500 Powell Rd, Wildwood FL
Cookie decorating, crafts and visits with Santa at the Wildwood Community Center, preceded by a quieter sensory-friendly hour. Free, all ages per the city.
Source: City of Wildwood Community Events; Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, December 19, 2026
Varies · Open to the public
Brownwood Paddock Square, The Villages
A neon-themed holiday night at Brownwood, Eastport and Spanish Springs. Located in The Villages. Time and cost were still listed as to be announced.
Source: The Villages, Seasons of Celebration calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Visit before you decide
The fastest way to know if a place fits is to be there on a real night. I am Cristian Gonzalez, a REALTOR® with eXp Realty, born and raised in Marion County and a Navy Veteran. I represent buyers independently, and I will plan the visit around what you want to see.
Tell me the dates you will be here. I will build a visit plan around these events, with Middleton's phases, the commute you care about, and homes worth a look.