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Last updated: November 11, 2024


Plan your perfect festive season in Gwynn Oak with our event guide. From residents to tourists, this guide is your gateway to the holiday wonders of Gwynn Oak.

Take a stroll through the enchanting German Christmas Village at Baltimore's Inner Harbor, where traditional crafts and festive treats set the scene for a delightful experience. Features like twinkling lights and authentic German cuisine highlight the rich cultural spirit of the holiday season. And the Miracle on 34th Street showcases a charming display of themed decorations and community spirit that you definitely don't want to miss. See more details on these and other fun events and activities below!

Contact information and details below.



Gwynn Oak Holiday Light Displays


What to Expect:

Local kids' tree decorations and community involvement.

Description:

The Grand Illumination of the Annapolis Tree is a festive event where local groups perform dancing and carols, and the annual Christmas Tree lighting ceremony includes carolers, music, and general merriment. Santa, Mrs. Claus, and Elfie join in to light the tree, making it a joyful celebration for all.

Where: Annapolis | More Info: Grand Illumination of the Annapolis Tree

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What to Expect:

Boats decorated with thousands of colored lights sail through Annapolis Harbor and Spa Creek.

Description:

The Eastport Yacht Club Lights Parade is an annual holiday event where boats decorated with thousands of colored lights sail through Annapolis Harbor and Spa Creek, creating a spectacular display of light and joy.

Where: Annapolis | More Info: Eastport Yacht Club Lights Parade

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What to Expect:

Community-driven holiday light display with resident-created decorations.

Description:

The Miracle on 34th Street is a 76-year-old holiday light display in Baltimore's Hampden neighborhood, featuring colorfully decorated homes, Christmas trees, trains, animated figures, and various holiday symbols.

Where: Baltimore | More Info: Miracle on 34th Street

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What to Expect:

Climate-controlled trolley ride with holiday music and local history insights.

Description:

Explore Baltimore's holiday lights and decorations on a guided tour through historic neighborhoods, including Harbor East, Fells Point, and Hampden.

Where: Baltimore | More Info: Holly Jolly Trolley

Event Organizer?

What to Expect:

Dazzling 75-foot tree with live music and festive activities.

Description:

Join CityCenterDC for its 10th Annual Holiday Tree Lighting, featuring a joyful music performance by The Revels, balloon artists, face painters, and holiday treats. NBC4’s Eun Yang will host the official tree lighting ceremony and countdown. Enjoy the dazzling 75-foot tree, visit the two resident 25-foot reindeer, and capture the holiday spirit with a photo under the Palmer Alley Dream Closet art installation.

Where: Washington D.C. | More Info: City Center Christmas Tree Lighting

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Gwynn Oak Holiday Markets and Shopping


What to Expect:

Extended shopping hours with holiday decorations and entertainment.

Description:

Downtown Annapolis transforms into a holiday shopping haven with Midnight Madness, featuring extended hours, holiday decorations, and entertainment along Main Street, West Street, Maryland Avenue, State Circle, Market Space, and Dock Street.

Where: Annapolis | More Info: Midnight Madness

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What to Expect:

Unique chocolate tour with diverse vendors.

Description:

The Annapolis Chocolate Binge Festival is a family-friendly event featuring chocolate vendors, holiday shopping, and live music. Enjoy a chocolate tour along West Street with various chocolate specialties and complete your holiday shopping at the local artisan market.

Where: Annapolis | More Info: Chocolate Binge Festival

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What to Expect:

Unique shopping experience with local artisans and live entertainment.

Description:

The Annapolis Holiday Market offers a variety of shopping, dining, and entertainment options in Historic Annapolis. Visitors can browse the work of 50 local artists, enjoy café dining, and experience live entertainment.

Where: Annapolis | More Info: Annapolis Holiday Market

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What to Expect:

Authentic German market with international vendors and festive food options.

Description:

German Christmas Village at Baltimore's Inner Harbor features over 60 vendors offering unique gifts and authentic European cuisine, including a wide selection of German mulled wine and traditional German food.

Where: Baltimore | More Info: German Christmas Village at Baltimore's Inner Harbor

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What to Expect:

Diverse local vendors and community activations.

Description:

The DowntownDC Holiday Market is a 20th-anniversary celebration in Penn Quarter-Chinatown, featuring upgraded vendor kiosks, diverse artisans, community activations, and a delectable food and beverage lineup.

Where: Washington D.C. | More Info: Downtown Holiday Market

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What to Expect:

Unique gifts and local artisanal goods in a festive holiday setting.

Description:

The Silver Spring Christmas Market and Holiday Craft Fair at Veterans Plaza offers a festive celebration featuring seasonal artisans, delicious treats, and the joyful spirit of the season. Explore a merry marketplace filled with handcrafted treasures from local artisans, savor delightful food and desserts from various vendors, and immerse yourself in the festive melodies of Christmas music.

Where: Silver Spring | More Info: Silver Spring Christmas Market and Holiday Craft Fair

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Gwynn Oak Holiday Shows and Entertainment


What to Expect:

Interactive holiday train ride with Santa and festive activities.

Description:

At the B&O Railroad Museum, join a two-hour immersive Polar Express experience where you'll dress in pajamas, enjoy a live performance of the Hot Chocolate song and dance, and receive the First Gift of Christmas—a silver sleigh bell—from Santa. Upon arrival at the North Pole, you'll enjoy crafts, make s'mores, shop for themed goodies, and have your picture taken with Santa. The event includes hot chocolate, sugar cookies, and live performances, with various seating options available.

Where: Baltimore | More Info: B&O Railroad Museum's Breakfast and Train Ride with Santa

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What to Expect:

Colorful floats and lively bands along a festive holiday route.

Description:

The Baltimore Mayor’s Annual Christmas Parade is a 2.5-mile route through Hampden and Medfield featuring colorful floats, local personalities, Darth Vader, the Boumi Shriners, lively bands, and culminating with Santa Claus, offering a delightful experience for the whole family.

Where: Baltimore | More Info: Baltimore Mayor’s Annual Christmas Parade

Event Organizer?

What to Expect:

Baltimore-inspired adaptation of A Christmas Carol with local actors.

Description:

In a 19th-century Baltimore setting, Chesapeake Shakespeare Company presents a fresh adaptation of Charles Dickens' A Christmas Carol. Gregory Burgess returns as Ebenezer Scrooge, navigating a journey from greed to redemption. This beloved tradition is infused with local charm and vibrant storytelling.

Where: Baltimore | More Info: A Christmas Carol at The Chesapeake Shakespeare Company

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Gwynn Oak Other Holiday Activities


What to Expect:

Ice skating with waterfront views of Baltimore's neon-lit skyline.

Description:

The Inner Harbor Ice Rink offers a festive ice skating experience with waterfront views of Baltimore's neon-lit skyline. Located at the top of the Amphitheater between the two Harborplace pavilions, it provides a unique setting for creating wintertime memories. The rink is open daily from November 11 to January 15, with regular hours of operation including Monday through Thursday from 12:00 p.m. to 10:00 p.m., Friday from 12:00 p.m. to 11:00 p.m., Saturday from 10:00 a.m. to 11:00 p.m., and Sunday from 10:00 a.m. to 8:00 p.m.

Where: Baltimore | More Info: Inner Harbor Ice Rink

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What to Expect:

Holiday celebration with zoo animals and activities.

Description:

Celebrate the holiday season at The Maryland Zoo with festive crafts, photo ops, special appearances, and more. Enjoy activities like train rides, story times, and scavenger hunts, all included with zoo admission or membership.

Where: Baltimore | More Info: Zoo Lights at The Maryland Zoo

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What to Expect:

Interactive science exhibits and hands-on activities.

Description:

Explore the wonders of science through interactive exhibits, planetarium shows, and hands-on activities at the Maryland Science Center. Engage with innovative exhibits ranging from astronomy to paleontology, and participate in workshops and live demonstrations.

Where: Baltimore | More Info: 12 Days of Science at Maryland Science Center

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