Dive into the Magic of Fall in St. Michaels!
Get Ready to Fall Head Over Heels for St. Michaels' Epic Harvest Festival – October 17-19, 2025!
Experience the thrill of autumn like never before in the charming Town of St. Michaels, where vibrant colors explode, and the air buzzes with excitement! Residents and businesses unite for the ultimate celebration of the season – Fall into St. Michaels – packed with non-stop fun for EVERYONE, from kids to furry friends!
Unleash Your Creativity in Town-Wide Contests!
Scarecrow Spectacular & Pumpkin Carving Extravaganza! Stroll the picturesque streets and marvel at jaw-dropping scarecrows adorning businesses and swinging from Talbot Street's telephone poles. Peek into shop windows for spine-tingling masterpieces from the pumpkin carving contest – who knows, you might spot the next viral sensation!
Bay Hundred’s Pumpkin Pie Showdown! Bakers of all ages, this is YOUR moment! Whip up three delectable pies for judging, then watch them fly off the shelves in a mouthwatering bake sale. All proceeds fuel awesome programs at the St. Michaels Community Center – taste victory and give back!
Paws-itively Adorable Pet Adventures!
Wag-O-Ween Dog Costume Contest! Dress up your pup for the cutest parade ever – think epic costumes, pro photos, and trick-or-treating at local spots! Last year's hit is back bigger and better, with proceeds powering the Talbot County Humane Society. Don't miss the fun – tails will be wagging!
Thrilling Jack Russell Races! Dog lovers, assemble! From speedy Jack Russells to the hilarious Dachshund Dash and the wild "So Your Dog Thinks He’s a Jack" category (for pups under 25 lbs), it's a barking good time! All dogs welcome to race or just mingle. Rain or shine, fuel up with coffee, donuts, a Bloody Mary & Mimosa Bar, and snag prizes in the 50/50 raffle from top local eateries and shops. Proceeds boost local dog charities – no dog? No worries, humans have a blast too! Pre-register your pup now for the races and join the pet party!
History Comes Alive!
St. Michaels Museum Walking Tours: Step back in time with captivating signature tours from the St. Michaels Museum at St. Mary’s Square. Reserve your spot today at www.stmichaelsmuseum.org – history never felt so alive!
Shop, Savor, Play & Stay in Paradise!
Indulge in St. Michaels' unbeatable vibe: World-class shopping in boutique havens, gourmet dining featuring fresh Chesapeake Bay delights, thrilling water adventures like kayaking and sailing, and cozy stays in waterfront inns or charming B&Bs. It's the perfect romantic escape or family adventure!
Plan Your Unforgettable Getaway NOW! Visit St. Michaels Tourism at www.stmichaelsmd.com for insider tips, bookings, and the full scoop. Don't just fall into St. Michaels – dive in and make memories that last a lifetime! 🍁🐶🎃
Also check out other Nonprofit events in Saint Michaels, Trips & Adventurous Activities in Saint Michaels.
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