The annual compendium of the season’s best events, attractions, and shopping. From shore to shore, across the Chesapeake Bay and back, we’ve organized the following events chronologically. Enjoy!
Christmas at Gaylord National
Experience the wonder of the season at Christmas at Gaylord National, running throughout the holiday season with dazzling displays, festive activities, and holiday shows for the whole family. Step into ICE!, where scenes from The Polar Express™ are brought to life through massive, hand-carved ice sculptures and colorful lights. Enjoy sweet treats, wintertime fun, and countless photo opportunities as you wander through a world filled with Christmas magic. Whether you’re visiting for the day or planning an overnight getaway, it’s the perfect way to make lasting holiday memories together. More info: christmasatgaylordnational.com
Photo by Russ Brown Photography
Christmas Village in Baltimore
Step into the festive charm of a traditional German-style market right in the heart of Baltimore. Through December 24, the Christmas Village transforms the Inner Harbor into a glittering holiday haven, open Sunday–Thursday from 12–8 p.m. and Friday–Saturday from 12–9 p.m. (closed Mondays and Tuesdays). Stroll through more than 65 vendors offering handcrafted gifts, ornaments, and seasonal treats, then warm up with mulled wine or hot chocolate as twinkling lights dance along the waterfront. It’s a merry mix of European tradition and Baltimore spirit—perfect for a holiday outing with family and friends. More info: baltimore-christmas.com
RiverArts Annual Holiday Show & Sale
Celebrate the season and shop local at the RiverArts Holiday Show & Sale continuing through December 22 in downtown Chestertown. Both the RiverArts Gallery and the Store at RiverArts will be filled with beautifully handcrafted works by local artists and makers—featuring fine art, pottery, jewelry, textiles, ornaments, and more. With a festive opening reception on December 5, this annual event invites you to find meaningful, one-of-a-kind gifts while supporting the creative community that makes the Eastern Shore shine. More info: mainstreetchestertown.org/event/riverarts-annual-holiday-show-sale
Lights on the Bay
Lights on the Bay returns to Sandy Point State Park through January 1, illuminating the shoreline with a spectacular drive-through light display that captures the magic of the season. This sparkling tradition features dazzling scenes, whimsical animations, and festive designs that delight visitors of all ages—all while supporting the SPCA of Anne Arundel County. Bring your family, friends, and even your furry companions, slip on a pair of 3D glasses to make the lights come alive, and enjoy an evening of holiday wonder along the Chesapeake Bay. More info: lightsonthebaymd.org
Winterfest of Lights Ocean City Maryland
Step into a twinkling wonderland at the Winterfest of Lights, where dazzling displays and holiday magic fill the air. Wander along the illuminated path through Northside Park, surrounded by thousands of sparkling lights and whimsical, animated scenes that celebrate the season. Warm up with a cup of hot chocolate, gather around the bonfire, or snap a festive photo with Santa before exploring the charming gift shop for one-of-a-kind finds. Families can enjoy crafts, games, and interactive displays scattered throughout the park—plus, pets are welcome on Wednesday evenings! Don’t miss the grand centerpiece: a breathtaking 50-foot Christmas tree that lights up the night with spectacular color and music. More info: ococean.com/Winterfest
40th Festival of Trees
The Tidewater Inn’s Gold Room in Easton transforms into a winter wonderland for the 40th Annual Festival of Trees, running Saturday, November 29 through Tuesday, December 2. Stroll through a dazzling forest of designer trees and wreaths, each one twinkling with creativity and community spirit. This beloved Eastern Shore tradition supports Talbot Hospice, offering a heartwarming way to celebrate the season while giving back. With festive displays, special events, and plenty of holiday cheer filling the weekend, it’s a shining example of how art, generosity, and tradition come together. More info: festival-of-trees.org
Central Maryland Chamber Holiday Mixer & Silent Auction
Kick off the holiday season with a night of networking and goodwill at the Central Maryland Chamber Holiday Mixer & Silent Auction on Wednesday, December 3, beginning at 5 p.m. at 8600 Foundry Street in Savage. Enjoy an evening of festive mingling with local business leaders, bid on exciting auction items, and toast to another year of community success. Proceeds from the event support the Chamber’s Educational Foundation scholarships, helping future leaders thrive. It’s a perfect blend of celebration, connection, and giving back—holiday spirit at its best. More info: web.centralmarylandchamber.org
Severna Park Annual Tree Lighting
Ring in the season with neighbors and friends at the Greater Severna Park & Arnold Chamber’s Tree Lighting at 1 Holly Ave. Expect sweet treats, festive tunes, and a quick, high-energy countdown to a sparkling evergreen that lights up the heart of town. It’s a simple, joyful way to kick off the holidays—bring the whole crew and keep an eye on the Chamber’s calendar for the exact time in December 2025. More info: gspacc.com/happenings-each-year
Midnight Madness
Downtown Annapolis comes alive under the glow of holiday lights during Midnight Madness, happening Thursdays, December 4, 11, and 18. From 4 p.m. to midnight (and until 11 p.m. on the final night), local shops open their doors late for an evening of festive fun and community spirit. Stroll the historic streets as carolers fill the air with music, twinkling décor sets the scene, and one-night-only specials make it the perfect time to check off your gift list. Whether you’re shopping, dining, or simply soaking up the small-town magic, Midnight Madness is Annapolis at its most charming. More info: downtownannapolispartnership.org/midnight-madness
Annual Dickens of a Christmas
Chestertown transforms into a scene straight from a Dickens novel on Friday and Saturday, December 5–6, as its historic downtown comes alive with old-fashioned charm and holiday cheer. Friday evening kicks off from 5 to 9 p.m. with twinkling lights, festive tunes, and cozy gatherings around fire pits, while Saturday brings a full day of merriment. Enjoy carriage rides, live music, local oysters, and appearances by Father Christmas himself as High Street fills with laughter and good cheer. It’s a magical celebration of community, tradition, and the timeless spirit of the season. More info: mainstreetchestertown.org/dickens-festival
The Festival of Trees
Celebrate the spirit of giving at Compass’s Festival of Trees (in loving memory of Mr. Bill Towers), taking place Friday through Sunday, December 5–7, at the Towers Family Historical Museum in Denton. The weekend begins with a festive Preview Party on Friday from 6 to 9 p.m., followed by free open houses on Saturday and Sunday that fill the museum with dazzling trees, community warmth, and holiday cheer. Proceeds benefit hospice and grief support services across Caroline, Kent, and Queen Anne’s counties, making this event as meaningful as it is beautiful. It’s a touching Eastern Shore tradition that celebrates life, memory, and the true heart of the holidays. More info: visitcaroline.org/event/festival-of-trees-2025
Centreville Christmas Parade
Bundle up for a small-town celebration as Centreville’s Christmas Parade steps off downtown on Friday, December 5, at 6:30 p.m. This year’s theme, “Bright Nights and Holiday Lights,” sets the stage for a festive evening of glowing floats, spirited marching units, and hometown pride in the heart of Queen Anne’s County. Gather along the route, cheer on your neighbors, and soak up the season’s magic as the community comes together for a holiday favorite. More info: townofcentreville.org
A Charlie Brown Christmas with Eric Byrd Trio
Relive the timeless charm of the Peanuts holiday classic as the Eric Byrd Trio brings Vince Guaraldi’s iconic A Charlie Brown Christmas score to life. Performances take place at Maryland Hall in Annapolis on Friday, December 5 at 6 p.m. and 8 p.m., and Saturday, December 6 at 6 p.m. and 8 p.m. This soulful, swinging jazz concert captures the warmth and nostalgia of the season, making it a perfect outing for families, music lovers, and anyone ready to embrace the holiday spirit. Experience the magic of Guaraldi’s melodies in a live performance that’s as heartwarming as the original special itself. More info: marylandhall.org
THE POLAR EXPRESSTM Train Ride
Climb aboard for a magical journey to the North Pole with THE POLAR EXPRESS™ Train Ride, running December 6–7, 13–14, and 19–23, with multiple departures each day. Families can sip hot chocolate, nibble on cookies, and enjoy live performances that bring this beloved story to life. Every passenger receives Santa’s First Gift—a shiny keepsake bell—as part of this immersive, pajama-friendly adventure that captures the wonder of the season. It’s a heartwarming holiday tradition sure to delight both the young and the young at heart. More info: borail.org/polar-express
Festival of Trains
The Queen Anne’s Railroad Society will host it’s annual Festival of Trains at the Kent Narrows Outlet Center in Chester on consecutive weekends, December 6–7 and 13–14. The event brings together many model train displays in several gauges, family activities (including a visit from Santa), and refreshments to enjoy. More info: facebook.com/qarrs
Glen Burnie High School Winter Craft Fair
Get into the holiday spirit while supporting local talent at the Glen Burnie High School Winter Craft Fair on Saturday, December 6 from 9 a.m. to 3 p.m. The school will be buzzing with creativity as artisans and makers showcase unique handmade gifts, perfect for everyone on your list. Shoppers can browse a bustling vendor hall filled with crafts, décor, jewelry, and seasonal treasures, all while enjoying delicious concessions and live music from the GBHS Music Boosters. It’s a festive day of shopping, community, and holiday cheer—where every purchase helps support the next generation of student musicians. More info: sites.google.com/aacps.org/glen-burnie-music/craft-fair
Vintage Christmas Market at Wildberry
Soak in the sights, sounds, and flavors of the season at the Vintage Christmas Market at Wildberry Farm + Market on Saturday, December 6. This charming outdoor event captures the cozy magic of the holidays with artisan vendors, live music, and festive bites set against a rustic countryside backdrop. Stroll through stalls brimming with handcrafted gifts, sip something warm (or something spirited) from the beer and wine garden, and take in picture-perfect holiday scenes around the farm. Whether you’re shopping for loved ones or simply savoring the season, this market is the perfect way to spend a December day. More info: wildberryfarmmarket.com
Easton’s Holiday Parade
Downtown Easton glows with holiday spirit on Saturday, December 6, as one of the Shore’s most beloved traditions takes center stage. The evening begins at 5:30 p.m. when Santa makes his grand entrance in Thompson Park, followed by the tree lighting at 6 p.m. and the parade stepping off at 6:30 p.m. More than 60 floats, marching bands, and community groups fill the streets with lights, music, and cheer, creating a night that captures the true magic of the season. Bundle up, bring the family, and join the crowd for this joyful Eastern Shore celebration. More info: discovereaston.com
Photo by Historic Annapolis
A Colonial Yuletide
Step back in time and celebrate the season 18th-century style at A Colonial Yuletide on Saturday, December 6 from 2 to 5:30 p.m. at the William Paca House & Garden and Hogshead sites. Wander through beautifully decorated historic settings alive with period music, costumed interpreters, and the sights and scents of a colonial Christmas. Families can enjoy hands-on crafts, sweet seasonal treats, and a festive atmosphere that captures the charm of Annapolis’s past. It’s a delightful way to experience holiday traditions of another era while making new memories in the heart of downtown. More info: annapolis.org/events/yuletide-2025
Tree Lighting Ceremony
For more than half a century, the Bowie Holiday Tree Lighting has brought neighbors together to celebrate the warmth and wonder of the season. On Saturday, December 6 at 7 p.m., the Bowie Senior Center will glow with festive lights, cheerful carols, and the excitement of Santa and Mrs. Claus arriving in style with help from the Bowie Volunteer Fire Department. Families can enjoy the countdown to the city’s sparkling tree, enjoy food and drinks, and share in a true community moment. Admission is free, but guests are encouraged to bring non-perishable food donations to help spread the holiday spirit to those in need. It’s a classic hometown celebration filled with joy, generosity, and plenty of seasonal sparkle. More info: cityofbowie.org
Gingerbread Festival
Sweeten your holiday season with the Gingerbread Festival, kicking off the Christmas in St. Michaels weekend from Thursday, December 11 through Sunday, December 14, 2025. Step into a sugary wonderland of whimsical creations as local bakers, artists, and families showcase their most imaginative gingerbread designs. Stroll through the displays, cast your vote for your favorite confection, and soak in the festive spirit that fills St. Michaels’ charming waterfront. It’s a delightful blend of creativity, community, and classic holiday cheer in one of the Shore’s most picturesque towns. More info: christmasinstmichaels.org
Annapolis Chocolate Binge Festival
Experience the sweetest celebration of the season at the Annapolis Chocolate Binge Festival, happening Sunday, December 7, 2025. Let your taste buds lead the way as the first block of West Street fills with chocolate vendors offering everything from truffles and caramel to brownies, cupcakes, and chocolate martinis. Stroll through the holiday market to discover handmade jewelry, pottery, candles, ornaments, and more from local artisans. Enjoy live music, festive entertainment, and the twinkling West Street Holiday Light Canopy as you treat yourself and shop for loved ones. Admission is $5 in advance, and tickets are expected to sell out—so don’t delay. More info: iwsannapolis.com
Holiday Open House at the Belair Mansion
Step into the season at the historic Belair Mansion during Bowie’s annual Holiday Happenings celebration. This festive open house welcomes visitors to explore the beautifully decorated 18th-century estate, filled with the sights, sounds, and scents of the holidays. Families can enjoy seasonal crafts, refreshments, and a touch of local history while taking in the elegant charm of Old Bowie in December. It’s a cozy, community-centered way to celebrate the season surrounded by tradition and holiday spirit. More info: cityofbowie.org/holidayhappenings
Nutcracker Tea 2025
Sip, savor, and celebrate the magic of the season at What’s Up? Media’s annual Nutcracker Tea on Sunday, December 7 at the DoubleTree by Hilton Annapolis. This elegant family event features a festive buffet, enchanting excerpts from The Nutcracker performed live on stage, and a special storytime with Santa and Mrs. Claus. Each seating is filled with holiday sparkle, delicious treats, and heartwarming moments that make it one of Annapolis’s most treasured holiday traditions. Perfect for families, friends, and anyone ready to revel in the beauty of the season. More info: whatsupmag.com/nutcracker-tea-2025
Annapolis Arts Alliance Toy Drive
Join the Annapolis Arts Alliance in spreading holiday joy now through December 20. The Alliance invites you to participate in its annual Toy Drive benefiting local children in need. Simply bring a new, unwrapped toy and drop it off during gallery hours at Gallery 57 West. Let your act of giving be part of something beautiful, because art lifts spirits, and so can you. More info: annapolis-arts-alliance.com
Elves for Elders
Spread a little extra holiday joy this season by joining Partners In Care’s heartwarming Elves for Elders program. On Thursday–Friday, December 11–12, between 10 a.m. and 2 p.m., volunteers are invited to deliver filled stockings to the Anne Arundel office and help brighten the holidays for local seniors. Each stocking—stuffed with thoughtful gifts, cozy treats, and personal touches—reminds recipients that they’re remembered and valued. It’s an easy and meaningful way to give back, whether you gather friends to assemble stockings together or make a solo delivery that sparks a smile. Community care has never looked (or felt) so festive. More info: partnersincare.org/elves
Magic Elf Hunt at Belair Mansion
Embark on a festive adventure at Belair Mansion’s annual Magic Elf Hunt on December 12 from 12 to 4 p.m. Santa needs help rounding up his mischievous elves, and young detectives are invited to join the search through the beautifully decorated halls of this historic mansion. Along the way, families will uncover hidden surprises, soak in the holiday cheer, and enjoy the joy of earning “official elf-hunter” status. Blending local history with playful imagination, this beloved tradition offers a merry afternoon of laughter, discovery, and Christmas magic for all ages. More info: cityofbowie.org
Oxford Holiday Market 2025
Celebrate the season Eastern Shore–style at the inaugural Oxford Holiday Market, running Friday–Sunday, December 12–14. This charming waterfront market invites visitors to shop juried artisans, discover one-of-a-kind gifts, and enjoy the cozy ambiance of this beloved small town. Hours are Friday 4–8 p.m., Saturday 10 a.m.–5 p.m., and Sunday 11 a.m.–4 p.m., giving you plenty of time to browse, dine, and soak up the spirit of the holidays. With delicious local food, festive tunes, and a visit from Santa himself, the Oxford Holiday Market is sure to become a new favorite tradition. More info: visitmaryland.org/events/oxford-holiday-market-2025
Christmas in St. Michaels 2025
The charming town of St. Michaels comes alive with holiday spirit during Christmas in St. Michaels, returning December 12–14. This beloved Eastern Shore tradition fills the waterfront streets with festive cheer, welcoming Santa, seasonal shopping, and joyful community events that capture the magic of the season. Visitors can also look forward to the release of the annual Limited Edition Collector’s Ornament, available in late September, with proceeds supporting local nonprofit organizations. Celebrate the spirit of Christmas, the beauty of giving, and the warmth of a community that shines brightest during the holidays. More info: christmasinstmichaels.org
Photo by John Parsons
Eastport Yacht Club Lights Parade
Get ready for one of Annapolis’s most dazzling holiday traditions—the Eastport Yacht Club Lights Parade—on Saturday, December 13 from 6 to 8 p.m. Watch as a fleet of brilliantly illuminated boats glides through Spa Creek and Annapolis Harbor, transforming the waterfront into a twinkling winter wonderland. Bundle up and find your perfect viewing spot along City Dock or Ego Alley, where nautical creativity shines bright against the night sky. It’s a sparkling celebration of community, craftsmanship, and Chesapeake cheer that truly defines the season. More info: eyclightsparade.org
The Nutcracker
Step into a world of magic and music with Ballet Theatre of Maryland’s enchanting production of The Nutcracker, running Saturday–Sunday, December 13–21, with multiple showtimes. This beloved Annapolis tradition brings Clara’s dream to life through fresh choreography, stunning costumes, and the unforgettable score of Tchaikovsky. With charming local touches and breathtaking performances, it’s a holiday favorite that delights audiences of all ages. Whether it’s your first time or a cherished annual outing, The Nutcracker promises an evening of elegance, wonder, and pure seasonal joy. More info: balletmaryland.org/nutcracker
Heroes Holiday Market
Find the perfect gift and support local makers at the lively Heroes Holiday Market, returning to Heroes Pub on December 14. This festive neighborhood favorite brings together 30-plus artisans offering handmade goods, holiday décor, and plenty of last-minute treasures. Guests can also enjoy tastings from Cane Collective and Gray Wolf Spirits, making it a true local experience filled with community spirit and holiday cheer. The event benefits The Chesapeake K9 Fund. More info: whatsupmag.com/events/heroes-holiday-market-0/
Mayor’s Christmas Parade
Baltimore’s holiday spirit takes to the streets at 1 p.m. on Sunday, December 14, when the 52nd Annual Mayor’s Christmas Parade marches down Falls Road and up The Avenue. Expect high-energy marching bands, colorful floats, neighborhood groups, and a wave from Santa as the route fills with music, laughter, and hometown pride. It’s big-city holiday energy with a beloved neighborhood feel—bundle up, grab a hot drink, and join the tradition. More info: themayorschristmasparade.com
Annual Kwanzaa Celebration
Honor tradition and community at the Annual Kwanzaa Celebration on Saturday, December 13 from 10 a.m. to 4 p.m. This vibrant event brings people together through music, storytelling, artmaking, and interactive cultural experiences centered on the Nguzo Saba principles. Families are invited to learn, create, and celebrate the values of unity, purpose, and creativity in an atmosphere filled with joy and reflection. It’s a day to honor heritage, strengthen community bonds, and carry forward the true spirit of Kwanzaa. More info: bdmuseum.maryland.gov
The Talent Machine Presents "A Merry Mix-Up" Holiday Spectacular
The Talent Machine Company’s annual Holiday Spectacular returns December 12–23 with A Merry Mix-Up, a festive musical revue that feels like stepping straight into the merry mayhem of the season. With both evening and matinee performances available, this family-friendly show is built for creating holiday memories—whether you’re making it a yearly tradition or discovering it for the first time. Expect a bright blend of your favorite holiday songs and dances, performed by an impressive cast of young entertainers ages 5 to 18 who bring huge energy, charm, and talent to every moment onstage. The fun doesn’t stop with the music, either: Rudolph, Frosty, the elves, and Santa himself make special appearances, adding extra sparkle and plenty of “did you see that?!” moments for kids (and the kids-at-heart). Tickets are $20, making it an easy, joy-filled way to wrap up a December day with a little wonder and a lot of cheer.
More info: talentmachine.com/shows
Photo by Cory Royster, courtesy of Military Bowl Foundation
Military Bowl 2025
Celebrate one of the region’s favorite college football traditions at the Go Bowling Military Bowl, kicking off at Navy-Marine Corps Memorial Stadium on December 27, at 11 a.m. This exciting postseason matchup pits teams from the Atlantic Coast Conference and the American Athletic Conference in a spirited game that honors and supports America’s service members. Organized by the Military Bowl Foundation, the event benefits Patriot Point, a retreat on Maryland’s Eastern Shore that provides rest and recovery for veterans, active-duty military, and their families. Enjoy high-energy football with a purpose as the community comes together to cheer, celebrate, and give back. More info: militarybowl.org
ASO’S Annual Holiday Pops Concert
Let the sounds of the season surround you at the Annapolis Symphony Orchestra’s Annual Holiday Pops Concert, a cherished musical tradition filled with festive cheer. Choose your perfect performance: Friday, December 19 at 7:30 p.m. at Maryland Hall in Annapolis; Saturday, December 20 at 3 p.m. at Severna Park High School; or Sunday, December 21 at 3 p.m. at Bowie State University. Each concert features holiday favorites, carols, and orchestral gems brought to life by the ASO’s world-class musicians. Expect sparkle, warmth, and a joyful celebration of music that captures the spirit of the season. More info: annapolissymphony.org
Santa’s Secret: Last Minute Holiday Extravaganza
Wrap up your holiday shopping in style at Santa’s Secret: Last Minute Holiday Extravaganza on Sunday, December 21, from 1:30 to 4:30 p.m. at Cult Classic. This free, family-friendly event features more than 20 local vendors offering unique gifts, crafts, and treats—perfect for those final touches on your holiday list. Kids can sip cocoa while adults enjoy a little seasonal “additive” as they browse and mingle. With a laid-back vibe, great finds, and community spirit, it’s the perfect way to end your holiday prep on a merry note. More info: visitqueenannes.com
New Year's Eve Annapolis Yacht Party
Ring in the new year with style aboard Watermark’s New Year’s Eve Annapolis Fireworks Cruise on December 31. This family-friendly evening on the water features music from DJ Lampdawg, a complimentary glass of bubbly for adults, cocoa for kids, and unbeatable views of the city’s fireworks display. Enjoy dancing, celebration, and the sparkling beauty of the Annapolis skyline as you toast to 2026. A full-service bar will be available with both alcoholic and non-alcoholic beverages. Even if the fireworks are canceled due to weather, the cruise will sail for a memorable night on the bay. More info: watermarkjourney.com
Ring in 2026! New Year’s Eve Events
As of press time, most details were still being finalized. Check with each municipality for updates. All events listed are for December 31.
Annapolis: 7 p.m. family fireworks, and midnight fireworks at Susan B. Campbell Park; annapolis.gov
Baltimore: midnight fireworks and drone show at the Inner Harbor; baltimore.org
Cambridge: New Year’s Boat Drop, midnight at the downtown waterfront; choosecambridge.com
Columbia: Symphony of Lights display and family friendly NYE fireworks at 7 p.m. at Merriweather Park at Symphony Woods; visithowardcounty.com
Easton: New Year’s Eve Crab Drop during First Night Talbot, 9 p.m. and midnight; eastonmd.gov
National Harbor: many restaurants, resorts, and attractions offer NYE specials and parties; nationalharbor.com
Rock Hall: New Year’s Eve Rockfish Drop and Hat Parade at Main Street and the Bulkhead; rockhallmd.com
Salisbury: live music, entertainment, activities, and more throughout downtown. Midnight ball drop; salisbury.md
Ocean City: midnight fireworks at Northside Park and on the beach at Dorchester Street; oceancitymd.gov
Washington, D.C.: entertainment and midnight fireworks on the National Mall; dc.gov
