Family events in Winter Park, FL

The Nostalgia Con Orlando is a fun, all-ages weekend bringing together cartoons and anime, video games, movies, TV shows, and comics. Expect live panels, cosplay, shopping, photo opportunities, and plenty of chances to relive favorite childhood memories with family and friends. Event hours run Friday 1:00 PM to 7:00 PM, Saturday 11:00 AM to 7:00 PM, and Sunday 11:00 AM to 6:00 PM, with special family admission details for Sunday.

Browse the Winter Park Farmers’ Market in the Central Park West Meadow area, a popular Saturday morning stop for fresh, locally grown produce, artisan breads and pastries, gourmet foods and spices, plants and flowers, and unique handmade crafts and gifts. It’s a great outdoor outing for the whole family, with free admission and nearby parking options, and leashed dogs are welcome. Since it’s outdoors, it’s weather dependent.

Families can discover art together at Rollins Museum of Art through a Family Studio designed for children ages 5 to 10 with an accompanying adult. Inspired by the museum’s current exhibitions, the experience combines interactive time in the galleries with a hands-on art activity. Registration is required and free, and it opens one month before the program.

At Lactation Station Florida, this hands-on class offers practical guidance for families who are bottle feeding exclusively, pumping, combining methods, or preparing in advance. The session is divided into two parts, beginning with how to choose an infant formula. Participants review the main types and what sets them apart, learn to interpret labels beyond marketing claims, consider cow’s milk based options, specialized blends and gentle varieties, recognize who each might suit or not suit, and identify signs that suggest discussing a change with a pediatrician. The second part focuses on bottle feeding skills, including how to select bottles and nipples and understand flow rate, how paced feeding supports babies, how to read hunger and fullness cues, positioning for calm feeds, how much and how often to offer while avoiding overfeeding, and safe preparation and storage for both formula and expressed milk. Combo feeding is addressed, along with facts about nipple confusion and steps to take if a baby refuses the bottle. Instruction is provided by Dr. Irissa Rosario, MD, a board-certified pediatrician with fifteen years of experience, and Giovana Rorato, IBCLC and owner of Lactation Station, combining medical insight with lactation expertise. Attendees compare real formula options side by side, handle different bottles and nipples, and practice paced techniques to leave with a clear, confident plan tailored to their baby and routine. There is time for questions, and snacks and tea are provided. The class is suitable for those expecting, returning to work, or already navigating feeding.

Celebrate connection, creativity, and confidence with a nurturing mother daughter spa experience designed to care for skin and strengthen bonds. Mothers enjoy gentle, holistic facials while daughters receive age appropriate mini treatments, all with clean skincare and soothing aromatherapy that encourage relaxation and a healthy glow. Herbal tea and light refreshments create a cozy pause for meaningful conversation. Guests craft a keepsake bracelet to remember the day, and there are rotating beauty themed projects such as blending a sugar scrub, assembling a scent roller, or making a lip oil for an extra touch of hands on fun. Guided moments invite positive affirmations, gratitude reflections, and thoughtful conversation starters, and families exchange handwritten notes that highlight self love and support. The setting is calm, safe, and welcoming, with activities that build confidence and create lasting memories. Ideal for mother daughter dates, birthdays, homeschool meetups, girls self care outings, and more. Suitable for moms and daughters ages 5 and up, and also wonderful for grandmothers and granddaughters. Advance appointments are required and walk ins are not accepted.

Relocating to Altamonte Springs at Hilton Orlando/Altamonte Springs, this collector show expands its floor space while keeping the same familiar focus on Star Wars and G.I. Joe. Vendors are dedicated exclusively to these franchises, featuring vintage and modern action figures, playsets and related collectibles. Attendees can look forward to special guest appearances and photo opportunities. General admission is listed at $10, with possible adjustments for early entry, and children under 12 are admitted free.

Tea time turns into meaningful connection at HealingMamaStudio with a luxury mother daughter gathering in a calm, spa inspired setting. Guests sip herbal teas and enjoy pastries and light refreshments while sharing guided moments that build confidence and spark heartfelt conversation. Activities include creating a keepsake bracelet, writing affirming notes to one another, and using affirmation cards to support bonding. An optional upgrade adds mini facials, lip gloss making, or beauty crafts for a fuller spa day feel. The experience is intimate and private, well suited for birthdays, grandmother and granddaughter outings, homeschool social time, mommy meetups, and weekend mother daughter dates. Families choose this Orlando experience for its focus on self love, wellness, and creativity. Private bookings are available and packages can be customized. Capacity is limited to preserve a boutique atmosphere, and advance purchase is required because walk ins are not accepted.

Survival Week at British Swim School features a Superhero theme and is integrated into regular lessons, giving swimmers the chance to practice essential water survival skills while wearing everyday clothes. The purpose is to understand how clothing feels in the water after an unexpected fall, then learn to stay calm, float, manage breathing, and reach safety in a closely supervised environment. Participants should wear a shirt and shorts or pants over their swimsuit, and superhero-inspired outfits are encouraged as long as they are comfortable and pool-safe, with capes optional. Goggles are not used during this week. Instructors lead level-appropriate survival exercises, answer safety questions, and share guidance for families on staying safe in and around the water at the school and elsewhere. The experience builds confidence in real-world situations, reinforces water safety rules for both children and parents, and offers a safe surprise-style scenario that is educational and fun.

Enjoy free, casual chess in the Oviedo Mall food court. Players of all ages and skill levels are welcome for informal games.

A private crafting session invites mothers and their children to slow down, connect, and make memories in a calm, holistic studio setting. Each 45 to 50 minute experience is guided and hands-on, with creative options that can include making candles or lip gloss, building vision boards, designing affirmation art or jewelry, and seasonal DIY projects. The format works well for small groups of 2 to 8 and suits mom and child dates, homeschool enrichment, birthday celebrations, girls day plans, time with grandma and granddaughter, or self-love centered creativity. Healing Mama Studio is a holistic space focused on mothers and daughters that also offers facials, tea parties, birthday parties, and self-care workshops for kids and moms. Advance purchase and registration are required and walk-ins are not accepted. Same day requests need availability confirmed ahead of time. Limited seating and small class sizes help ensure each child receives personal attention.

Discover the basics of Dungeons & Dragons, Warhammer, board games, and other tabletop favorites in beginner-friendly sessions. Open to all ages, this event features an experienced staff member who provides instruction, runs practice games, and answers questions throughout the session so newcomers can learn and play with confidence.

Catch a family-friendly live performance by The Wiggles for “Tree of Wisdom Spectacular” with an early show at Hard Rock Cafe Orlando. Seating options are available in several sections, with different ticket prices depending on where you sit. Children under 12 months don’t require a ticket for entry, but they do need to sit on a parent or guardian’s lap.

Designed for toddlers and preschoolers ages 3 to 5, this heart-centered crafting class in Orlando offers a calm, supportive space for young artists to explore creativity while building fine motor skills, confidence, and social connections in a small group. Each 45-minute session features an age-appropriate themed project with sensory-friendly materials, and activities rotate to keep things fresh, including seasonal crafts, simple painting, sensory art, bracelet or keepsake projects, beginner beauty-safe DIY, and holiday-inspired creations. Pricing is $25 for a single drop-in or $79 for a monthly membership, with membership benefits that include priority seating, steady social development, structured weekly creativity, and savings on classes. Advance registration is required and walk-ins are not accepted, and same-day booking requests should be confirmed by text before arriving.