Photo courtesy Chesapeake Bay Maritime Museum
Your Week of Fall Fun is Here!
From clever comedy to pumpkin-filled adventures, this week is packed with events that bring the season to life! Catch the sharp wit and hilarious drama of ART at Everyman Theatre, or pick the perfect pumpkin while supporting The Light House at the beloved Pumpkin Patch for a Purpose. Sip and savor at Brampton 1860’s “Grape Expectations” dinner, dazzle at Zachary’s Jewelers Mark Henry Trunk Show, or celebrate Halloween with a festive Pumpkin Walk, Harvest Fest, and the Wildberry Halloween Market. Oyster lovers won’t want to miss the All You Can Eat Oyster Roast or OysterFest at the Chesapeake Bay Maritime Museum, while music fans can enjoy an international tour of sound with Chesapeake Harmony’s Musical Journey. End the week giving back on the greens at Birdies for Benedictine. Whatever your vibe—arts, food, family fun, or giving back—there’s something this week to make your autumn sparkle!
'Art' by Yasmina Reza translated by Christopher Hampton and directed by Noah Himmelstein
October 22nd – 25th; Everyman Theatre, Baltimore 7:00pm – 8:30pm
Get ready for sharp wit, clever banter, and a friendship put to the ultimate test in Yasmina Reza’s Tony Award-winning comedy ART. Set in modern-day Paris, this brilliantly funny play dives headfirst into what happens when one friend buys a wildly expensive, all-white painting—and the others can’t quite see the “art” in it. What begins as a simple disagreement spirals into a hilarious exploration of taste, loyalty, and ego as three longtime friends unravel decades of camaraderie over a single blank canvas. Smart, biting, and irresistibly entertaining, ART proves that sometimes the biggest masterpieces—and messes—are found in friendship itself.
Friends of The Light House
October 23rd, 24th; St. Martin’s Evangelical Lutheran Church, Annapolis 2:00pm – 6:00pm
Each fall, the spirit of community and giving fills the air as Annapolis organizations come together for the beloved Pumpkin Patch for a Purpose. This cherished local tradition invites families and friends to pick out fresh, beautiful pumpkins while supporting The Light House—a vital homeless prevention and support center serving our community. Open Thursdays and Fridays from 2–6 PM and weekends from 10 AM–6 PM, the patch is more than just a place to grab your perfect pumpkin. Stay for the games, photo ops, and festive fall fun that make this event a highlight of the season. Every pumpkin purchased helps light the way toward ending homelessness—one joyful visit at a time.
"Grape Expectations": A Playful Plates Party at Brampton 1860
October 23rd; Brampton Inn, Chestertown 6:00pm – 8:00pm
Get ready for a hauntingly elegant night at the manor! Step inside a 19th-century estate where fine wine, gourmet bites, and a touch of mischief set the stage for an unforgettable evening. “Adult Trick or Treat Night” transforms dinner into an indulgent five-course adventure, featuring southern-style favorites with a spooky twist—each paired perfectly with bold, flavorful wines. Sip, savor, and mingle as wine expert Monica Connors guides guests through each pairing, unlocking a world of flavor in a setting brimming with old-world charm. Whether you’re joining for dinner or making it a full overnight escape, this spirited soirée promises an experience as rich and unforgettable as the season itself.
Zachary's Jewelers Mark Henry Trunk Show
October 24th – 26th; Zachary Jewelers, Annapolis
Step into a world of color, creativity, and sparkle with Mark Henry — where every gemstone tells a story. Known for their use of rare Brazilian treasures like Alexandrite, Paraiba Tourmaline, and Moonstone, this collection redefines luxury with a modern, playful twist. From vibrant hues to bold, reimagined classics like Ruby, Emerald, and Sapphire, each design captures the perfect blend of timeless elegance and contemporary edge. Whether you’re drawn to color that pops or diamonds that dazzle, these pieces are made to turn heads and start conversations. Discover your next statement piece and experience the brilliance of Mark Henry’s artistry. Register for free and explore the magic of color redefined.
Pumpkin Walk
October 24th; Hammond Harwood House, Annapolis 4:00pm – 6:00pm
Celebrate the spooky season in style at the annual Pumpkin Walk! This beloved Annapolis tradition invites families to the historic Hammond-Harwood House for a day of fall fun, games, crafts, storytelling, snacks, and a festive costume parade around the mansion. Kids can enjoy face painting and a short, family-friendly mansion tour that unveils colonial-era superstitions and the home’s unique architecture. Don’t forget your costume—there’s a selfie station perfect for capturing those autumn memories! This year’s event gets an extra dose of magic as Frolic the Fox joins the fun, leading the parade and enchanting little ones with songs, stories, and playtime in the garden. With beer and wine available for adults, it’s a celebration the whole family will love—full of laughter, imagination, and a sprinkle of Halloween magic.
Bags, Bingo & Bourbon
October 24th; Pip Moyer Recreational Center, Annapolis 5:00pm
Join the Annapolis Police Foundation for an evening where community and camaraderie take center stage! Bingo, bourbon, and good times await at the Pip Moyer Recreation Center, where guests can enjoy a hearty spaghetti dinner, lively games, and a chance to win big. With raffles, door prizes, silent auctions, pull tabs, and special rounds for designer purses and bottles of bourbon, there’s fun for everyone. Dinner and drinks will be served throughout the night, with a full cash bar available. Proceeds from the event support the Annapolis Police Foundation’s efforts to strengthen local law enforcement and fund vital community programs—making every laugh, sip, and shout of “Bingo!” a win for the city.
Bountiful Harvest - SAVE THE DATE
October 24th; The Atreeum at Soaring Timbers, Annapolis 6:00pm – 11:00pm
Get ready for an unforgettable evening of great food, lively music, and community spirit at the annual Annapolis Light House Benefit! Guests will enjoy gourmet dining, an open bar, live entertainment, and an exciting auction — all in support of a vital local cause. Proceeds from the event directly benefit The Light House, Annapolis’s homeless prevention and support center, helping individuals and families rebuild their lives through housing, job training, and essential resources.
Halloween Field Market at Wildberry
October 25th; Wildberry Farm + Market, Crownsville 9:00am – 1:00pm
Celebrate fall on the farm at Wildberry’s outdoor Halloween Market! Stroll through a festive lineup of local small businesses offering handmade goods, seasonal treats, and farm-fresh finds. Enjoy a hot breakfast and coffee from the Wildberry Farm to Table Food Trailer while you shop, and don’t forget to come in costume — kids (and adults!) can trick-or-treat their way through the market. Plus, enjoy free Halloween-themed balloon animals, furry friends on leashes are welcome, and admission is completely free. It’s the perfect way to spend a crisp autumn morning surrounded by community, creativity, and a little Halloween magic. Rain date: Sunday, October 26, 9 a.m.–1 p.m.
Celebrate Tench Tilghman Week
October 25th; Talbot County Free Library, Easton 10:00am
Step back in time and explore the fascinating story of the Tilghman family during the Revolutionary War — a family divided by loyalty but united by love. Colonel Tench Tilghman served as George Washington’s longest-standing aide-de-camp and trusted patriot, while his father, James Tilghman, remained loyal to the British Crown. His uncle, Matthew Tilghman, became known as the “father of the revolution in Maryland,” and one of his brothers even served in the British Navy. Through this captivating look at Maryland’s history, discover how the Tilghman family managed to maintain deep bonds of respect and affection despite standing on opposite sides of the war. Their story — and the lessons learned from George Washington’s example — offers timeless insights into empathy, unity, and understanding during times of great division.
Harvest Festival
October 25th; Pip Moyer Recreation Center, Annapolis 10:00am – 2:00pm
Calling all ghouls and goblins! Get ready for a spooktacular time at Harvest Fest. Enjoy free family fun with a spooky magic show, face painting, hay rides, a pumpkin patch, and Trunk-o'-Treating. Come celebrate with costumes, candy, and community fun. This year’s festival will feature favorite characters like Bluey, Glinda and Elphaba from Wicked, Princess Tiana, Spider-Man, Miles Morales, and Rumi from K-Pop Demon Hunters. Harvest Fest will take place on Saturday, October 25, from 10 a.m. to 2 p.m. at the "Pip" Moyer Recreation Center. Registration for this event is required. Code: 3296.
OysterFest
October 25th; Chesapeake Bay Maritime Museum, St. Michaels, 10:00am – 4:00pm
The Bay’s favorite bivalve takes center stage at CBMM’s OysterFest on Saturday, October 25, from 10:00 a.m. to 4:00 p.m. Enjoy oysters served in a variety of ways, plus local food, craft beer, spirits, live music, and family fun. Highlights include an oyster stew competition, cooking demos, and children’s activities. Guests can also shop local vendors, sample Chesapeake delicacies, and join the popular oyster slurp-off contest. CBMM members receive discounted admission. Free parking and shuttle service will be available from St. Michaels Middle/High School. For safety, non-service dogs and outside alcohol are not permitted.
Rock ‘N’ Roll Bash
October 25th; The Recher, Towson 6:00pm
Rock ‘N’ Roll all night for a cause at the 22nd Annual Rock ‘N’ Roll Bash, presented by CFG Bank, on Saturday, October 25th at The Recher! This high-energy event isn’t just about great music — it’s about making a meaningful difference for children and families in need. All proceeds from the Bash benefit the Casey Cares Foundation, which provides uplifting programs and lasting memories for critically ill children and their families throughout the Mid-Atlantic region. Headlining this year’s show is High Voltage, the nation’s premier AC/DC tribute band, bringing the full-throttle energy and excitement of a live AC/DC concert to the stage. Join us for an unforgettable night of music, community, and compassion — and help keep the good times rolling for families who need it most.
All You Can Eat Oyster Roast
October 26th; Kent Island Resort, Kent Island 1:00pm
Get ready for an oyster lover’s dream at Kent Island Resort! Enjoy a laid-back afternoon by the berm and firepit, where all-you-can-eat oysters, live music, and good vibes take center stage. Savor the fresh-off-the-grill flavors and soak up the crisp autumn air in a setting that’s equal parts rustic and relaxing. Looking for a little extra indulgence? Try the decadent Casino and Rockefeller oysters, available for purchase onsite, and pair them with refreshing drink specials for the perfect coastal feast. Best of all — every shell gets a second life! All oyster shells will be recycled to help restore the Chesapeake Bay.
Chesapeake Harmony Presents a Musical Journey
October 26th; Historic Baldwin Hall, Millersville 2:00pm – 4:00pm
Take your senses on a trip around the world at Musical Journey – Explore the World Through Music! Enjoy an afternoon filled with captivating live performances and global flavors, as local ensembles bring the sounds of different cultures to life. Sample delicious bites inspired by cuisines from across the globe while you sit back and enjoy the show. Performances include the Chesapeake Harmony Chorus, Bearfoot Quartet, 2nd Star Quartet, and Moscato Quartet — each adding their own unique flair to this international celebration of music. Beer and wine will be available for purchase (21+ with valid ID)
Birdies for Benedictine
October 28th; Talbot County Club, Easton
For more than 30 years, the Benedictine Charity Golf Classic has been more than just a day on the greens — it’s a tradition of giving, camaraderie, and community impact. Over the decades, this beloved tournament has raised more than $1 million to support Benedictine’s life-changing programs for children and adults with developmental disabilities and autism. Golfers, sponsors, and supporters alike come together each year for a day of friendly competition, shared purpose, and generosity that truly makes a difference. Every swing, putt, and sponsorship helps provide the essential resources, education, and care that empower individuals to reach their fullest potential. Stay tuned for registration and sponsorship details — and get ready to tee up for an incredible cause!
