Fall fun is officially in full swing around the Chesapeake! Kick off October with everything from coffee crawls and fall festivals to waterfront celebrations, local markets, live entertainment, and plenty of family-friendly fun. Spend the weekend cuddling donkeys, shopping local art and vintage finds, cheering on cyclists, or celebrating with your four-legged friends. Whatever your perfect fall weekend looks like, there’s plenty happening around the area to fill your calendar!
Café Diem: The Annapolis Coffee Crawl
September 28th – October 4th; Restaurants/Cafe’s in and Around Annapolis, Annapolis
Sip your way through Annapolis during Café Diem: The Annapolis Coffee Crawl! Spend the week exploring local coffee shops, cafés, restaurants, and happy hour spots while sampling everything from lattes and specialty brews to espresso martinis. Follow the self-guided crawl to discover new favorites, support local businesses, and earn chances to win prizes along the way. Coffee lovers, consider this your excuse to caffeinate your way around town!
Partners In Care End-of-Summer Luau
October 1st; Kurtz’s Beach, Pasadena 5:30pm
Say aloha to the end of summer at the inaugural Partners In Care End-of-Summer Luau! Enjoy an island-inspired evening filled with tropical cuisine and drinks, music, cornhole, auction items, and plenty of festive fun. Meki’s Tamure Polynesian Arts Group will bring the islands to life with authentic Polynesian dance, colorful costumes, rhythmic drumming, and thrilling fire dancing. Best of all, the celebration supports Partners In Care and its work helping older adults age in place with dignity, purpose, and community support.
Odenton Fall Harvest Festival
October 2nd -4th; Odenton Volunteer Fire Department, Odenton 5:00pm
Kick off October with some classic fall fun at the Odenton Fall Harvest Festival! Bring the family out for kids’ carnival rides, festival food, and plenty of seasonal fun throughout the weekend. Admission is free, making it an easy outing for families looking to get into the autumn spirit. Proceeds from the festivities benefit the Odenton Volunteer Fire Company and its service to the community.
You're a Good Man, Charlie Brown
October 2nd; Annapolis Mall, Annapolis 7:30pm
It’s the final weekend to catch Charlie Brown, Snoopy, Lucy, Linus, and the rest of the Peanuts gang in You’re a Good Man, Charlie Brown! This award-winning musical brings the beloved comic strip to life with catchy songs, childhood adventures, and plenty of heartwarming moments celebrating friendship. Catch one of the final performances Friday, October 2nd at 7:30 p.m.; Saturday, October 3rd at 2 or 7:30 p.m.; or Sunday, October 4th at 2 p.m. Don’t miss your last chance to enjoy this nostalgic and fun-filled show!
Homestead Gardens Fall Family Weekends 2026
October 3rd – 4th; Homestead Gardens, Davidsonville 10:00am
Make some room on your fall calendar for Homestead Gardens’ Fall Family Weekends! Enjoy a day packed with pony rides, hayrides, pumpkins, barnyard animals, inflatables, live music, seasonal treats, and plenty of activities for the whole family. The fall fun continues every Saturday and Sunday through November 1st, giving you plenty of chances to join in. Grab the kids and make some autumn memories at this favorite seasonal tradition!
Boom Ball
October 3rd; Prince Georges County Stadium, Bowie 5:00pm
Get ready for a whole new spin on baseball when Boom Ball takes over the ballpark! Expect fast-paced action, unexpected rules, big personalities, and nonstop entertainment designed to keep the energy going from the first pitch to the final out. Arrive early for BOOM Fest before the opening ceremonies and game get underway. Stick around after the action for a fireworks show to cap off the night
Galesville Maritime Festival 2026!
October 3rd; West River Sailing Club, Galesville 2:00pm
Celebrate the Chesapeake traditions that continue to shape Galesville at the Galesville Maritime Festival! Explore this historic working waterfront with a boat parade, narrated tours on the West River, a farmers market, traditional fishing demonstrations, museum access, and hands-on maritime activities for kids. Live music and local food will add to the festivities while boatyard tours and local history offer a closer look at the community’s maritime roots. Bring the whole family for an afternoon celebrating life on the water and Galesville’s unique heritage!
Hoedown on the Farm
October 3rd; Maryland Therapeutic Riding, Crownsville 4:00pm
Kick up your boots for a feel-good evening at Maryland Therapeutic Riding’s Hoedown on the Farm! Enjoy BBQ, live music and dancing, games, activities, and plenty of family-friendly fun while experiencing the welcoming MTR community. Proceeds support equine-assisted services for children and adults of all abilities, veterans, active-duty military members, first responders, and their families. Come for a night on the farm and help make the healing power of horses accessible to more people in the community!
Donkey Cuddling
October 3rd; Campbell’s Lane Farm, Easton 9:00am
Slow down and spend some quality time with the sweetest four-legged friends at Donkey Cuddling! Meet the gentle herd at Campbell’s Lane Farm, where guests of all ages can pet, brush, cuddle, or simply relax alongside the donkeys. This heartwarming farm experience is all about taking a break from the hustle and enjoying the calming connection that comes from spending time with animals. Bring the family and get ready for plenty of adorable donkey time!
Annapolis First Sunday Arts Festival w/ The Accidental Poet!!
October 4th; West Street and Calvert Street, Annapolis 11:00am
Spend your Sunday strolling through downtown Annapolis at the First Sunday Arts Festival! Browse more than 150 artists, makers, and vendors while enjoying food trucks, live music, outdoor dining, and plenty of local creativity along West and Calvert streets. Stop by Author Alley to meet The Accidental Poet and hear stories read aloud for festivalgoers of all ages. It’s a fun, family-friendly way to shop local, discover something new, and enjoy a fall day downtown!
Naptown Flea
October 4th, MRE Mercantile, Annapolis 10:00am
Naptown Flea is popping up in Eastport for the first time! Shop more than 20 local vintage sellers, small businesses, and creators for one-of-a-kind finds while supporting the local community. Make a day of it with an Eastport scavenger hunt that encourages you to explore even more neighborhood businesses along the way. Whether you’re hunting for vintage treasures or just looking for a fun Sunday outing, there’s plenty to discover
Together in TEAL Annapolis
October 4th; Annapolis Mall, Annapolis 8:30am
Come together for a meaningful morning at Together in TEAL Annapolis! Walk or run alongside ovarian cancer survivors, caregivers, families, and supporters while helping raise awareness and funds for the National Ovarian Cancer Coalition. The event celebrates the strength of the TEAL community while supporting programs, education, and resources for those impacted by ovarian cancer. Sign up in advance and take steps toward making a difference for survivors and their families!
Beagle Rescue of Southern Maryland's Beagle Bash Fundraiser
October 4th; Crownsville Canine, Crownsville 11:00am
Bring your four-legged friends out for a tail-wagging celebration at Beagle Rescue of Southern Maryland’s Beagle Bash! This year marks the rescue’s 25th anniversary, with more than 100 dogs expected to join the fun alongside a fenced play area, raffles, treats for pups and people, photos with Snoopy, and a doggie costume contest. Meet adoptable dogs looking for their forever homes and connect with fellow beagle lovers throughout the day. Every wag, raffle, and registration helps the rescue continue saving, caring for, and finding homes for dogs in need!
Anne Arundel County Lifeline 100 Bicycle Event
October 4th; Kinder Farm Park, Annapolis 7:00am
Get ready to ride at the 12th Annual Lifeline 100 Community Bicycle Event! Cyclists of all ages and abilities can choose their own adventure, from a kids bike rodeo and family fun ride to 15- and 30-mile trail rides or scenic 65- and 100-mile routes through Anne Arundel County. Riders with special needs and bikes of all kinds are welcome, making this a truly inclusive day on two wheels. Even better, proceeds support local nonprofits, with the event raising more than $450,000 for the community since it began!
