Whether you’re decking the halls, getting crafty, or checking in with Santa … there’s something extra special about Christmas in the Heart of Chesapeake country. From the Crab Basket Tree and Christmas parades to musical performances and the “deadrise” New Year’s Eve boat drop, make it a Maryland Eastern Shore holiday season! Visit our events calendar for a complete listing of all events and details.

And, if you’re look for a place to curl up and relax – or need room for visiting friends and family – take advantage of off-season rates at hotels and B&Bs! Our friends at the Hyatt Regency Chesapeake Bay have a “Home for the Holidays” deal. From now through January 31, enjoy exclusive rates: Sun-Fri $109 and Sat $129. Call 410-901-1234 to learn more.

Events Calendar

Ho-Ho-Holiday Fun, Santa Sightings & Festive Lights

Lighted Boat Parade – Deck your hulls – or be dazzled by the decorated boats! – at the Christmas Lights on the Choptank Boat Parade on November 25 (rescheduled from Nov. 24 because of weather) starting at 4:45pm in Cambridge Creek, past Long Wharf to Great Marsh Park and back.

A Cambridge Christmas – Ring in the holidays Thanksgiving weekend at the Christmas Tree Lighting at Spring Valley at the Court House on November 25 (rescheduled from Nov. 24 because of weather).  5pm Fountain Rededication and 5:30pm Tree Lighting. Music by the Maple Elementary Marching Band and Community Mass Choir.

Christmas Train Garden – Gaze in wonder at Cambridge’s train display downtown every day in December. For more than 80 years, volunteers with the Cambridge Rescue Fire Company have created this spectacular train garden for the holidays. Sneak peek Nov. 25 right after the Tree Lighting. Open daily, Dec. 1-31, Mon-Fri, 6-9pm and Sat & Sun 1-4pm and 6-9 pm. Free (monetary donation or canned food donation welcome).

Santa in Downtown Cambridge – Visit with Santa in Cannery Way (brick courtyard in the 400 block of Race Street in Downtown Cambridge) from 3 to 8pm on Dec. 1, 8, and 15.

Santa’s North Pole Vault – Katie Mae’s Restaurant has turned what was once a bank vault into a spot for Santa! He’ll be stopping by regularly starting Saturday, Dec. 1 from 12-2pm. Then Fridays (Dec. 7, 14, 21) from 6 to 8pm and Saturdays (Dec. 1, 8, 15, 22) from 12 to 2pm.

Cambridge-Dorchester Christmas Parade – Be dazzled by light, sound and sights of one of Maryland’s largest nighttime parades starting at 5pm on Saturday, Dec. 1. Celebrate 70 Years of Christmas Cheer as marching bands, floats, classic cars, horses and Santa fill Downtown Cambridge’s streets for this beloved holiday happening!

Crab Bushel Tree Lighting – In five short years, Cambridge’s Crab Basket Tree has become one of the Shore’s favorite holiday destinations for family photos! Gather round the tree Dec. 1 before the Cambridge-Dorchester Christmas Parade for the official lighting at 4:45pm. Marvel at 200 crab baskets used to make this holiday wonder in the Craig’s Drug Store parking lot. You can also watch volunteers build the tree all day long on Nov. 23 (weather permitting)

Christmas Open House at Mowbray’s Garden Center – Pick out your Christmas tree, visit with Santa from 10am-Noon or browse the holiday gift shop at Mowbray’s holiday winterland Dec. 1, 9am.

Free Holiday Movies – Cambridge Premier Cinemas hosts a FREE Holiday Movie Series. Enjoy Christmas classics and holiday fun every Saturday and Sunday in December. Fun for the whole family! Most movies start at 10:30am.

Breakfast with Santa – Enjoy a scrumptious breakfast buffet featuring Santa at River View at the Point Sunday, December 2 at 8:30am. Every child receives a personalized gift. Reservations required. Call 410-228-0870.

Festival of Wreaths – Pleasant Day’s 19th annual Holiday Benefit Gala and Festival of Wreaths is December 6 in Cambridge. Doors open at 5:30pm. Featuring handcrafted wreaths, entertainment, refreshments, silent auction and more. Call 410-228-0190.

Breakfast with Santa at Water’s Edge – Have Breakfast with Santa at the Hyatt’s Water’s Edge Grill on December 8, 15 and 22.

Cookies with Santa – Enjoy cookies with Santa at the Hurlock Volunteer Fire Company Auxiliary on December 8, 2-4 pm, with the Hurlock Christmas Parade starting at 5pm.

Hurlock Christmas Parade – Begins at 5pm on December 8. The theme is “Tis the Reason for the Season.”

Old Fashioned Christmas Second Saturday – Stroll the streets of Downtown Cambridge Dec. 8 for a festive, family affair. Hear carolers, attend a music recital at 447, or the Ginger Cats at Black Water Bakery. Stop by the Dorchester Center for the Arts’ Gallery of Gifts and reception. Visit with Santa at Katie Mae’s during the day and Cannery Way, 5-8pm. Bundle up for carriage rides through Downtown from Simmons Center Market. Visit DowntownCambridge.org for updated schedule.

Spaghetti with Santa – Enjoy all-you-can-eat spaghetti plus a visit with the Santa on Dec. 13 from 4:30 to 7:30pm, hosted by the Dorchester County Technology and Career Center’s Teacher Academy. Storytime, too!

Winter Wonderland Music and Tree Festival – Enjoy a magical winter wonderland as Governor’s Hall is decked with a grove of festively decorated trees on Dec. 15 from 5 to 9pm at Sailwinds Park. Christmas chorus musical, silent auction, pictures with Santa, and refreshments. $5 Admission.

Christmas Cookie Wine Pairing – Head to Layton’s Chance Winery for tasty pairings of four different Christmas cookies and four different wines. December 16.

Downtown Santa Trail – Downtown Cambridge’s merchants are excited to launch a new festive tradition. Come downtown Dec. 15 from 3 to 7pm to track down Santa. Follow and collect clues to learn Santa’s location. Use your secret password to meet and visit with Santa! Treats and kids’ activities at every stop. Fun for the whole family

Firemen’s Festival of Trees – See beautiful trees, bid on your favorites, and bring the kids for hands-on crafting fun at Santa’s Workshop on Dec. 15 at the Hurlock Volunteer Fire Co.

Luminaria Night Celebration – Glowing luminarias line the streets of Vienna, a 300-year-old town on the Nanticoke River, Dec. 15, 5 to 8pm, for this treasured holiday tradition. Historic homes and churches open their doors for tours, music, refreshments, and old-fashioned hospitality. Free. Tickets are $5 for home tours.

Cookies with Santa at 447 – Groove Theatre Company hosts a visit with Santa, complete with story reading, Christmas card making, and photos with Santa at 447 in downtown Cambridge. Dec. 21 from 4 to 7pm.

Santa at Cabin Fever Play Centre – Santa will visit Cabin Fever on Dec. 23 from 1 to 4pm. Sweet treats available. 442 Race Street in Downtown Cambridge.

Music & Performances

Jazz in the Sanctuary – Waugh Chapel hosts the Jazz in the Sanctuary Band from Baltimore, an afternoon of jazz-inspired Christmas music Dec. 9 at 4pm. $20 donation includes light fare.

Holiday Concert with Chorus of Dorchester – The Chorus of Dorchester presents a free holiday concert on Sunday, Dec. 9 at 6pm at Christ Episcopal Church and Dec. 11 at 7pm at the Dorchester Center for the Arts.

The Nutcracker – The Eastern Shore Dance Academy presents “The Nutcracker” at 6pm on Dec. 15 and 3pm Dec. 16 at Cambridge-South Dorchester High School in Cambridge. The dancers perform under the artistic direction of Jessica Hindman-Wheatley.

Christmas Choral Concert – The Christ Church Concert Series features a Christmas Choral Concert with the Tidewater Singers on Sunday, Dec. 16, 4pm. $10 for adults/free for students. Reception follows in the parish hall.

Bluegrass Nutcracker – Dreading another season of canned Christmas music? Get in the spirit with a sizzling, bluegrass-steeped bar-for-bar rendition of Tchaikovsky’s Christmas classic with Front Porch Orchestra on Dec. 21 at 447 Gallery in downtown Cambridge.

Harriet Tubman Tour, Dinner & Show – Experience a custom tour, storytelling by local historians of the area, Harriet Tubman re-enactor and a home-cooked meal during a special event with Harriet Tubman Tours on December 22.

DIY Fun: Getting Crafty

Many of these workshops expect to sell out, so reserve your spot as soon as you can!

Holiday Take-N-Make – Dorchester Career and Technology Center hosts an all-day workshop Friday, Nov. 30, 9am to 7pm. Make an evergreen centerpiece, boxwood tree, wreath or ornament. Good for children of all ages. Holiday music and light fare.

Classic German Holiday Baking – Discover new holiday baking traditions, or re-trace ones from your past! Join Matchcoat Sojourner and Germany native, Nikki Phelps for a three-hour journey that includes a hands-on class and tastings Sat. Dec. 1, two classes, one at 9am and one at 1pm.

Mommy & Me Make and Take – Join Caterpillar Kids on Dec. 2 at 1pm for a ‘wellness’ workshop. Children will make and keep a jar of sleep time bath salts and mom (or dad!) a wellness roller. Light snacks and refreshments. $10 Fee covers parent and child.

Holiday Mixed Greens Wreath – Make a Holiday Mixed Greens Wreath at the Blue Awning on Dec. 2, 1pm or Dec. 6, 5:30pm. All wreath making supplies provided. Bring a pair of clippers and garden gloves.

Sangria and Wreath Making – Enjoy an afternoon of Sangria and Fresh Christmas Greens at Mowbray’s Garden Center December 2 or 9, 3pm. Materials and instructions on making a 14″ Fresh Mixed Green Wreath. Class includes sangria, small plate appetizers, wreath materials and lots of holiday cheer!

Mimosas & Mistletoe – Holiday decorating does not feel complete without the wreath hung on the door! Join Layton’s Chance Winery for a morning of wreath making on Dec. 8 from 11am to 1pm.

Fresh Cemetery Arrangement Class – Remember your loved ones in a special way this holiday season by creating a cemetery arrangement at Mowbray’s Garden Center at 10am on Dec. 16.

Giving Thanks & Giving Back

Dorchester Santa Toy Drive – Donate a new toy for a local child in need. There are several drop-off locations at businesses; check the Dorchester Santa Toy Drive Facebook page for the latest list. The drive ends Dec. 8 with a festive finale at RAR Brewing from 12pm until closing time at 1am.

Wreaths Across America – Help place wreaths on the gravestones of veterans at the Eastern Shore Veterans Cemetery at 10am on Dec. 15 and donate to help buy the wreaths here.

New Year’s Eve & New Year’s Day

All Day Yoga – Get ready for a healthy and relaxed new year with a daylong yoga and meditation practice at Anahata Yoga in Cambridge. Dec. 31, 10-3 pm.

New Year’s Eve Deadrise Drop – Join in the celebration in Downtown Cambridge as folks gather to watch a small replica of a deadrise – the traditional waterman’s boat – travel down 70 feet of track at midnight to ring in 2019.

First Day Hikes – Welcome a recent New Year tradition – the “First Day Hike” – in two of the Heart of the Chesapeake’s most beautiful settings on Tues., Jan. 1. Choose from either the Harriet Tubman Underground Railroad State Park & Visitor Center (10am and 1:30pm) or Blackwater National Wildlife Refuge (10am). Reservations required. Visitor Centers will be open until 5pm and hot drinks and light snacks will be served.

Find details on all these happenings on our online calendar!

Events Calendar

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