Top 10 Holiday Events to Kick Off the Season This November

CALIFORNIA, Md. – Ready to get in on that holiday feeling early? We’ve got the events for you! While most holiday-themed events don’t start until Dec. 1, some local places have decided to start the fun early. Here are the top 10 events to check out.

Holiday Craft Fair — Huntingtown High School, Huntingtown, Md.
From 9 a.m. to 3 p.m. on Nov. 17, 2024, “Join us for a festive day of holiday shopping with over 75 unique vendors! Enjoy food trucks, sweet treats, and fun activities for the whole family. Meet Santa and the Grinch and let the kids get creative at our craft station. Don’t miss out on basket raffles and more!” Admission is free. For more information, visit the event’s Facebook page.

Top 10 Holiday Events to Kick Off the Season This November Pink Friday: A Celebration of Small Business in Solomons
Photo Credit: A Celebration of Small Business in Solomons

Pink Friday: A Celebration of Small Business in Solomons — Solomons, Md.
From 12 p.m. to 8 p.m. on Nov. 22, 2024, “Get ready to kick off the holiday season with our 2nd Annual Pink Friday—a celebration of local shopping and a whole lot of fun! Forget the big box stores, and join us for a full day of giveaways, prizes, and fabulous finds right here in Solomons!” The day begins with a free tote and game card at AllyCat Boutique, then you make your way through local shops with fun activities along the way. At the end of the event, participants are invited to a Simply Social Event for a fun photo op! For more information, visit the event’s Facebook page.

Annual Holiday Bazaar — American Legion Stallings-Williams Post 206, Chesapeake Beach, Md.
From 9 a.m. to 3 p.m. on Nov. 23, 2024, “Join us for the Annual American Legion Auxiliary Holiday Bazaar! There will be baked goods, a kids’ craft table, Santa, raffles, and vendors galore. A delicious lunch will also be available for purchase.” For more information, visit the event’s Facebook page.

It’s Fall, Y’all ‘Sip and Shop’ — Mully’s Brewery, Prince Frederick, Md.
From 1 p.m. to 6 p.m. on Nov. 23, 2024, “Enjoy a pint of your favorite Mully’s brew and do some shopping from local vendors! The market will be open with plenty of products to browse, and we’ve got food covered; everyone’s favorite, Cousins Maine Lobster, will be on-site for your lunch and dinner needs.” For more information, visit Mully’s Brewery’s event page.

Pictures with Santa and Toys for Tots Toy Drive — Prime Time Children’s Youth & Activity Center, Owings, Md.
From 1 p.m. to 3:30 p.m. on Nov. 24, 2024, “Join us for our annual Toy Drive event! Bring a toy (or two) and receive a picture with Santa or the Grinch!” This event is a great opportunity for holiday photos of the kids! For more information, visit the event page.

Top 10 Holiday Events to Kick Off the Season This November Thanksgiving Day Turkey Trot 5K — Jefferson Patterson Park
Photo Credit: Thanksgiving Day Turkey Trot 5K

Thanksgiving Day Turkey Trot 5K — Jefferson Patterson Park, St. Leonard, Md.
Starting at 7 a.m. on Nov. 28, 2024, “Come strut your stuffing with us at the Calvert County Community Partners Turkey Trot 5K! This is a family-friendly, fun-filled race through Jefferson Patterson Park and a long-standing tradition for Project Echo since 2012.” Day-of registration costs $50. For more information, visit Project Echo’s website.

Top 10 Holiday Events to Kick Off the Season This November Garden In Lights — Annmarie Sculpture Garden & Arts Center
Photo Credit: Annmarie Sculpture Garden & Arts Center

Garden In Lights — Annmarie Sculpture Garden & Arts Center, Solomons, Md.
From Nov. 29, 2024, to Jan. 1, 2025, from 5 p.m. to 9 p.m., with some exceptions (listed on the website), “A must-see holiday tradition for the entire family! Enjoy a stroll through the gardens to see the magical holiday lights display. There will also be holiday shopping, festive exhibits, and food available for purchase at on-site food trucks.” Tickets range from $18 to $24, depending on whether you buy ahead of time on their website. For tickets and more information, visit the Annmarie Garden website.

Christmas on the Square — Downtown Leonardtown Square, Leonardtown, Md.
Beginning at 4:30 p.m. on Friday, Nov. 29, 2024, “The holiday season begins in Leonardtown when Santa arrives for Christmas on the Square and the Annual Tree Lighting Ceremony in the town square. With holiday music, entertainment, sleigh, train, and hay rides, live nativity, balloon arts, and so many other fun activities! This beloved annual event is free and open to the public.” Some streets downtown will close during the event. For details on closures and everything Christmas on the Square, visit the event’s website.

Top 10 Holiday Events to Kick Off the Season This November Evening Tides: Candlelight Christmas at Piney Point Lighthouse
Photo Credit: Candlelight Christmas at Piney Point Lighthouse

Evening Tides: Candlelight Christmas at Piney Point Lighthouse — Piney Point, Md.
From 5:30 p.m. to 7:30 p.m. on Nov. 30, 2024, “Join us for a festive holiday evening on the grounds of the beautiful historic park at Piney Point Lighthouse Museum featuring candlelight, carolers, a hot chocolate bar, letters to Santa, Buddy the Elf, and the return of the Annual Building Bricks Lighthouse Challenge!” Local gifts will also be available for purchase at the museum gift store. Admission is $5 per person. For more information, visit the event’s Facebook page.

Bubby’s Christmas Farewell — Flat Iron Farm, Great Mills, Md.
From Nov. 29 through Dec. 23, 5 p.m. to 9 p.m., located at 45840 Hwy to Heaven Ln. “Join us for a heartfelt farewell at Flat Iron Farm as we celebrate Bubby Knott’s legacy during this beloved holiday tradition.” This year’s theme is “Giving Back,” with a goal to raise $100,000 for local charities in honor of Bubby’s spirit of community support. Entry is free, with exciting activities for everyone! Charity drives and cash donations will be accepted, ensuring that all proceeds benefit Bubby’s favorite causes. Enjoy dazzling Christmas lights, photos with Santa Claus, local food trucks, entertainment and music, craft vendors, a petting zoo, pony rides, family-friendly activities, a hot chocolate and s’mores pit, a Christmas market, and weekly special events. For more information, visit the event’s Facebook page.

So, whether it’s one of these events or you’re creating traditions of your own, we hope your holiday season is filled with lots of love, fun, and cheer!

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Samantha McGregor is a devoted writer and longtime resident of Chesapeake Beach, Maryland, where she’s lived since the age of four. With a love for her community, Samantha gravitates toward stories that...

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