Events


December 3–Midnight Madness Shopping

_DSC8139View our lovely Christmas Video here!

Date: Saturday, December 3, 2022
Location: Talbot Street and throughout the town shopping area

Each year, the town of St Michaels is transformed into a picture perfect holiday postcard, the shops, restaurants and B&B’s are decorated with stunning greenery, lights and festive cheer.

The holiday spirit is felt throughout town, which makes coming to St. Michaels during the holiday season a special experience, year after year, and provides a wonderful backdrop to shop for the holidays.

More details HERE!

December 9-11–Christmas in St. Michaels

Golden_2013 Parade 9Christmas in St. Michaels is celebrating its 36th year of fundraising festivities with the return and expansion of its weekend of holiday events taking place on the water and in the heart of historic St. Michaels, Md. this Dec. 9-11. This year’s events include a Lighted Boat Parade and festive Talbot Street Parade; a Tour of Homes; Breakfast with Santa; Holiday Music and Meals; a Santa Dash; a Marketplace and Sweet Shoppe, and a Light up the Night drive-by house and harbor tour.

The goal for this year’s Christmas in St. Michaels events is to raise funds to distribute grants to local beneficiaries. More than 25 family services, education and child development, and community enhancement organizations depend on Christmas in St. Michaels funds to support their programs and activities.

The Marketplace and Sweet Shoppe located at St. Mary’s Square’s Granite Lodge kick off the weekend event at noon on Fri., Dec. 9. Proceeds from every sale benefit local nonprofits, with shoppers finding one-of-a-kind, artisan-crafted items and culinary delights available only during this weekend event. The Marketplace and Sweet Shoppe are open for select hours through Sun., Dec. 11 at 3:00 p.m.

Holiday music will fill the air throughout the weekend event, including music provided by Christ Church St. Michaels beginning at 4:30 p.m. on Sunday. A complete list of entertainment will be provided on Christmas in St. Michaels’ website.

Family-favorite events include Saturday’s Breakfast with Santa for children ages 4 to 9 years old, which takes place from 8-10:00 a.m. at the waterfront Foxy’s Harbor Grille, with limited $10 tickets available for online purchasing. The 10:30 a.m. Talbot Street Parade, Santa Dash, and beginning of the Tour of Homes are wonderful mid-day events, with the Lighted Boat Parade beginning along St. Michaels Harbor at 6:00 p.m. Parade routes, event details, online tickets, and more are at christmasinstmichaels.org.

“We love to see local people and those from throughout the Mid-Atlantic return to our events year after year, especially for our homes tour,” says Christmas in St. Michaels Board President Pat Martin. “Christmas in St. Michaels includes one of Maryland’s longest-running home tours and features beautifully decorated homes in our historic district and among the area’s wide expanses of country and watersides.”

The Tour of Homes takes place during select hours on Saturday and Sunday, with limited tickets available for advanced online purchase. The $25 per person ticket includes a one-time admission to all tour homes; transportation to the countryside homes; a detailed tour guide booklet with local information, detailed home and other major St. Michaels landmark descriptions; and free admission to the Chesapeake Bay Maritime Museum, the Classic Motor Museum, and the St. Michaels Museum at St. Mary’s Square for Saturday and Sunday.

Christmas in St. Michaels’ Old Fashioned Eastern Shore Christmas Dinner takes place on Sat., Dec. 10 starting at 11:00 a.m. and lasting until 3:00 p.m., or when the meals are sold out. Dinners include sliced roast turkey, Maryland fried oysters, and a large assortment of sides and desserts. The event will be held at the Union United Parish Hall on Fremont Street in St. Michaels with dine-in and carry-out dinners available at $20 per person, with tickets sold at the door, on the day of the event.

This year’s 19th Christmas in St. Michaels Collector’s Ornament features the Maryland Blue Crab and is adapted from an original drawing by local designer and artist Scott Sullivan. In 1989, the Blue Crab (Callinectes sapidus) was designated the Maryland State Crustacean and is the state’s most valuable commercial fishery. The Limited-Edition Ornaments are packaged in a keepsake box and are available for purchase at select area stores and on the Christmas in St. Michaels website beginning Sept. 25.

Christmas in St. Michaels began in 1987 when a group of energetic volunteers recognized the need for daycare services in the community. Funds were raised through community support, and a daycare center was established, now known as Critchlow Adkins Children Centers. Sponsors and patrons of Christmas in St. Michaels since that time have helped raise more than $1.4M in support of numerous local non-profit organizations.

Proceeds from Christmas in St. Michaels help the people served by local non-profit organizations. Event updates, online purchases, and more about Christmas in St. Michaels are at christmasinstmichaels.org.

February 12-14–Valentine’s Day and Winter Romance

St. Michaels Xf V-day 300x600Winter is a very romantic time in St. Michaels! Cozy inns, elegant and relaxed dining, wonderful shops (many with lovely jewelry, hint, hint.)
Watch a Winter Romance video here!

LIKE our Facebook page!

Visit our calendar of events page!

Plan your visit here!

Here are some of the things they are saying about us:

“My day to day life is very stressful and I don’t really have a lot of time to relax. I finally got a weekend off and my boyfriend surprised me with a romantic weekend getaway to St. Michaels. The owners were extremely nice and helpful. They gave us the best tips for our weekend and were very accommodating. We had room 1 on the first floor. It was cozy with a king size bed, very comfortable, and nice little fireplace for the evening. We did not have a tv in our room which was absolutely amazing for getting away. However, there was a tv in the lounge area with dvd’s, plenty of books to read and complimentary coffee, hot tea, cider, hot chocolate, and little pastries. Each morning we awoke to the amazing smells coming from the kitchen and warm voices for conversation. The food was incredible. Fresh ingredients all prepared each morning. I really appreciate the care they put into everything. They shared stories about the history of the town and we always had an abundance of conversation. The town was quaint and beautiful with a lot of neat little stores and excellent cuisine. Weather was great with a slight breeze from the water. We will definitely be back.”


“My choice for a weekend winter escape! No Crowds! Shopping, Cafés, Museums, Pubs & Saloons, all with no crowds! ENJOY!”

March TBD–ChocolateFest


Date: Saturday, March TBD, 2023
Website and tickets: HERE

The 5th Annual St. Michaels ChocolateFest will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts. Our inns and bed and breakfasts will feature chocolate inspired get-away packages.

The Chocolate Crawl will take place on Saturday, March TBD, 2023 from 11:00 a.m. – 4:00 p.m. throughout the town of St. Michaels at participating businesses and restaurants. Chocolate lovers will enjoy shopping throughout town sampling amazing artisan chocolates, desserts, locally crafted wine, beer and spirits.
Purchase Tickets Here.

March 17–St. Patrick’s Day

Shopping CartEvery year on March 17, the Irish and the Irish-at-heart across the globe observe St. Patrick’s Day. What began as a religious feast day for the patron Saint of Ireland has become an international festival celebrating Irish culture with parades, dancing, special foods and a whole lot of green.

St. Michaels is joining the St. Patrick’s Day celebration with special events. The annual Carpenter Street Saloon shopping cart races are held every year on St. Patrick’s Day at Midnight. Proceeds benefit the St. Michaels and Tilghman Fire Departments.

Participating businesses will have specials all weekend long.

Buy a personalized shamrock to adorn the street! $50 each to support the St. Michaels Police Department “S.M.Y.L.E” Program (St. Michaels Youth Law Enforcement) which is a great program which educates kids about law enforcement.

April to November—Farmers Market

Market

Click here to watch a video about the St. Michaels Farmers Market

Follow the Farmers Market on Facebook

When: Saturdays starting in April, 2023, from 8:30am-11:30am

Where: 206 S. Talbot Street St. Michaels MD (between Knotty Living and Pemberton Pharmacy)
Market opens with special precautions

Saturday rain or shine, with the first hour reserved for our most vulnerable customers. Public parking lot next to Pemberton’s. Local fruit, vegetables, meat, eggs, flowers, booze, and more, all grown or made within a 60-mile radius. Our vendors are all eagerly awaiting the opening of the Market season and we might even have a few new vendors in our Pop-up Tent…..come check it out.

It takes a village and WE NEED YOU!
EMAIL: stmichaelsmarket@gmail.com

June to September, Thursdays, 6 p.m.–Summer Concerts in the Park – See you again in 2023!

Location: Muskrat Park on Green Street
Times: June to September, Thursday nights from 6-7:30 p.m.

If it’s summer, it’s Summer Concerts in Muskrat Park. These free Thursday night concerts are sponsored by the St. Michaels Community Center. So, bring a chair or a blanket and a picnic and enjoy our beautiful waterfront park and great music!

Please, no alcoholic beverages in Muskrat Park.

June TBD, 2023—CBMM Antique & Classic Boat Festival & the Arts at Navy Point

18992671425_c8f2ee549a_oDates: Friday & Saturday, Father’s Day Weekend, June TBD, 2023
Fri. 10am – 5pm; Sat., 10 am-5 pm: Sunday, 10 am-3 pm. Entrance included with CBMM general admission – tickets valid for two consecutive days.
Location: Chesapeake Bay Maritime Museum, 213 N. Talbot St., St. Michaels, Md.
Ticket Prices:
• $6 Admission for CBMM Member
Non-member pricing:
• $18.00 Adults
• $15.00 Seniors 65+ & college students with ID
• $14.00 Retired military with ID
• $6.00 Kids 6-17
• $6.00 Active Military (with ID)
• Free for Children ages 5 and under

VIEW EVENT PHOTOS HERE!

Wooden and fiberglass classics, vintage racers, and other antique and Chesapeake Bay-related boats are returning to the Chesapeake Bay Maritime Museum for the 35th Antique & Classic Boat Festival and the Arts at Navy Point in St. Michaels, Md.

Hosted by the Chesapeake Bay Chapter of the Antique & Classic Boat Society, this Father’s Day tradition brings a sense of nostalgia to the Miles River and CBMM’s docks and campus, drawing some of the area’s finest classic boats, nautical and maritime treasures, and entertainment to the waterfront festival.

This year’s festival celebrates a theme of Cruising on the Chesapeake, with classic-style cabin and express cruisers and sport fishing boats expected to attend, and a full slate of boating history seminars planned on June __ & __. Click here to see a list of planned seminars.

The show attracts everything from the finest runabouts to yachts, and includes race boats, work boats, launches, hydroplanes, and utilities. Chris-Craft, Trumpy, Gar Wood, Donzi, and Lyman are among some of the names represented with sizes ranging from a 9-foot hydroplane to 70-foot plus cruisers. Several Jersey Speed Skiffs—a crowd favorite—will be displaying their aptly named strengths throughout the show.

“With a juried competition among entrants for best restored and preserved boats, this festival attracts the best of the best when it comes to classic and antique boats,” said ACBS-Chesapeake Bay Chapter Festival Chairman Bob Hamilton. “We’re thrilled the festival is able to return to CBMM’s beautiful campus this summer and can’t wait to see the public there.”

From Friday, June TBD, through Sunday, June TBD, the festival’s signature Arts at Navy Point pavilion brings juried fine artists, craftspeople, and vendors to CBMM’s waterfront campus, offering nautical and maritime-themed items for boat and home. Festival hours are 10am–5pm Friday and Saturday, with the Arts at Navy Point and limited displays continuing on Sunday from 10am–3pm. Entrance to the festival is included with CBMM’s general admission, which is good for two days and free for CBMM members.

Festival parking and a Saturday shuttle service are free, with CBMM a short walk to specialty shops, restaurants, inns, bed & breakfasts, and other attractions in St. Michaels’ historic district. For information about the Antique & Classic Boat Society’s Chesapeake Bay Chapter, visit chesapeakebayacbs.org.

REMINDER: For safety reasons, non-service dogs need to be kept home during CBMM festivals, including the Antique & Classic Boat Festival & the Arts at Navy Point. Carry-on alcohol from dock or land is prohibited.

For more information, call 410-745-2916 or visit CBMM.

July TBD, 2023, 7-10pm – Big Band Night

In celebration of Independence Day, the Chesapeake Bay Maritime Museum on the Miles River in St. Michaels, Md. welcomes The Shades of Blue Orchestra for a live performance at its Saturday, July TBD, Big Band Night. The St. Michaels fireworks are scheduled to launch after dusk that evening, with CBMM’s waterfront campus a great venue from which guests can enjoy the fireworks. The rain date for the concert and fireworks is Sunday, July TBD.

The orchestra is set to begin at 7pm, with the public invited to bring lawn chairs and picnic blankets for an evening of music, dancing, and fireworks along the Miles River. Food, ice cream, and non-alcoholic beverages will be available for purchase during the event, which is generously sponsored by Eastern Shore Tents & Events.

Mixing together popular standards, a variety of musical styles, and dance-able rhythms, the Shades of Blue Orchestra combines brass, woodwind, and rhythm instruments to bring music from the 1930’s to present to the Miles River. Established in 1976, this 18-piece Big Band consists of a well-balanced complement of brass, woodwind, and rhythm instruments, as well as two of the finest Big Band vocalists anywhere.

CBMM’s Welcome Center will open at 6p for Big Band Night guests to enter the campus for the event. Admission to Big Band Night is $6 for CBMM members and $10 for non-members, with children ages 5 and under, plus active and retired military, free. After 8:45pm, admission will be reduced to $2 for those watching the fireworks only. Advanced tickets and more information are at https://bit.ly/CBMMBandNight.

July TBD, 2023, 10:30 a.m. — Classic Motor Museum Pre-Independence Day Parade

A 1929 Model A Roadster leads the way and was among the favorites at the Classic Motor Museum parade in St. Michaels.

The CMM is excited to announce the Annual Classic Motor Museum Pre-Independence Day  Parade will be held on Saturday, July TBD, 2023 from 10:30 am – 11:30 am! The participants will line up at Perry Cabin Park, and will head down Talbot St, pausing for the emcee to announce the make, model and driver of the vehicle, through the rest of town, and ending the parade at the Museum at 102 E Marengo St. Where Cars & Coffee will be held, along with refreshments available for a small donation.

There is a cap on registrations, so be sure to get registered today HERE!!!

For information about events and programs of the Classic Motor museum, visit www.classicmotormuseum.org.