Eastern Shore Vacation Rentals

17th annual St. Michaels Concours d’Elegance on Chesapeake Bay & 8th Annual Chesapeake Bay Motoring Festival
2024-06-08 08:00 - 2024-09-29 16:00 (America/New_York) | MD
Kent Island Yacht Club will host two prestigious events this year – the 8th annual Chesapeake Bay Motoring Festival on June 8-9, and the 17th annual St. Michaels Concours d’Elegance on Chesapeake Bay on September 27-29. Both events are presented by St. Michaels Concours d’Elegance on Chesapeake Bay.

Venue:
Kent Island Yacht Club

The event features a special invitational class of racing Corvettes sponsored by Cunningham Automotive to celebrate Corvette’s 71st anniversary, a do-over from last year’s event which was hindered by Tropical Storm Ophelia.
The Grand Marque of the show is the sleek and elegant Delahaye, with a spotlight on Chesapeake Bay yachting. Entrant registration is free, with an application process for Concours, both available online.

St. Michaels Concours d’Elegance Chair Luke L. Phipps expressed excitement about the Kent Island Yacht Club’s ideal location, making both events grand celebrations of motoring excellence on Maryland’s Eastern Shore. Phipps highlighted the inclusion of locally sourced cuisine, craft libations, vendor tents, live music, and awards ceremonies throughout the weekend events.
Both events are open to the public, and attendees are encouraged to arrive by boat, with dockage available at the Kent Island Yacht Club and Hyatt Place Marina. Limited slips are available, and advanced reservations can be made by contacting info@smcde.org.
See event updates and more, including entrant registration, early-bird discounted tickets, and more at www.smcde.org.
See less

Organizer:
Event by St Michaels Concours d’Elegance and Chesapeake Bay Motoring Festival – TM

Easton's Farmers Market
2024-06-15 08:00 - 2024-12-21 13:00 | MD
The Easton Maryland Farmers Market has been operating for over 40 years.
Located in the municipal parking lot in the 100 block of North Harrison Street the pedestrian-only market features live music every Saturday at 10:30.
All of our vendors are cultivating, producing, cooking and crafting their inventories so be sure to stop by and support your local farmers, producers, and artisans.
The market is open 8am-1pm Saturdays only.
Venue:
114-126 N Harrison St, Easton, MD, United States, Maryland 21601
Organizer:
Event by Easton Maryland Farmers Market

Easton Trivia Nights at Doc's Downtown Grille
2024-06-18 07:00 - 2024-10-15 21:30 | MD
Let’s Do Trivia! is a weekly, team-based, live-hosted pub and restaurant trivia game show.
FRIENDS * FOOD * FUN!
FREE TO PLAY – BIG PRIZES TO WIN!
$40 First Place + more!
Our team-based trivia game is perfect for groups of friends, family, or co-workers. Let’s Do Trivia! gives you time to answer questions while also enjoying food, drink, and conversation with your people.
One member of each team will use a smart phone or tablet to register the team and answer questions.
Our games are hand-crafted each week by a team of writers and checkers to guarantee 99.99% accuracy.
Our host venues are the best at providing great food and service as well as value for your money. Ask a server about food or drink specials
Venue:
Doc’s Downtown Grille
Organizer:
Event by Let’s Do Trivia
View the website for all dates:
https://www.facebook.com/events/980831212988277/980831282988270/

Old School R&B Crab & Cruise in Crisfield
2024-06-22 16:30 - 2024-09-28 21:30 | MD
Get ready for the ultimate seafood extravaganza of the summer!
This event has premium crabs measuring 6 1/4″ up to 8″! 97.5FM DJ, Big Mark will be mixing up the R&B/Hip Hop hits from 90’s and 00’s on the upper level of the cruise while music plays on the lower level.
Hurricane Hazel will be providing crab-picking demos during the feast portion. It’ll be a fantastic day in the Crab Capital of the World.
See why it’s called the Baddest Crab Party on the Bay.
Choose from the ‘Crab-Feast ONLY’ ticket or the all-inclusive ‘Crab AND Cruise’ ticket: https://crabandcruise.com/
MUST BE 21 TO ATTEND THE EVENT
Other events going until Sep 28th 2024 visit the website!
https://www.crabandcruise.com/shop-detail?productId=vRlE3AVHq&fbclid=IwZXh0bgNhZW0CMTAAAR1Y2gAEMddzQj2dL9VIxhbk7_UqTOeO5DGVqfOLdjrjMvIj3p8FtEWY0vs_aem_AV2n0DoAw3zcr5HJBpy0hB-LR0hJHA9rmdV9wKvAO9BzguA761Hl-4IfYMIo23jRcIFIo6LSXycLQYS2BEUXWWY7

First Friday of the Month Gallery Walk in Downtown Easton
2024-07-05 17:00 - 2024-10-04 19:00 | MD
On First Friday the art galleries of downtown Easton extend their hours and invite you on a tour of artistic adventure – openings, lectures, book signings, and more!
View new art exhibits, meet the artists, and discover sales and great deals.
Enjoy dinner and drinks at one of our restaurants, stroll downtown, and spend the entire First Friday evening in beautiful downtown Easton.
Event by Discover Easton
Venue: Downtown Easton, MD

Food Truck Night In Queenstown
2024-07-19 16:00 - 2025-02-21 19:00 | MD
Food truck night supporting the Queenstown Volunteer Fire Department Auxiliary! Skip a night cooking and grab your dinner from one of our local vendors, starting at 4pm. Weather dependent, you can dine with us or take your food to go. We will be having these once a month during the summer months, so be sure to check back to see what vendors are coming to each.

Venue

Queenstown VFW Auxiliary

7013 Main Street
Queenstown, MD 21658 United States

Website:
https://www.facebook.com/events/188962950625263/188964257291799/?event_time_id=188964257291799&ref=newsfeed

Monthly Bingo in Easton
2024-07-20 13:00 - 2024-10-19 16:00 | MD
Lunch available doors open at 12
Venue: 29511 Canvasback Dr, Easton, MD 21601-7141, United States
Event by George Willey

Emily's Produce In Cambridge
2024-07-27 09:00 - 2024-12-16 17:00 | MD
Join the start of our 25th Season on Thursday April 11th!

We’ll be opening our doors and showcasing our commitment towards a LOCAL, Healthy, and Sustainable way of living – the Emily’s way!

Venue:
2214 Church Creek Rd., Cambridge, MD, United States, Maryland 21613

Organizer:
Event by Emily’s Produce

Time & Date:
April 11th starting at 9am to Close

Academy Art Museum in Easton
2024-07-27 10:00 - 2024-11-26 19:00 | MD
WHERE ART IS
FOR EVERYONE
Welcome to the Academy Art Museum!
Plan your visit with us and discover something new.

OPEN TODAY 10:00 AM
–
7:00 PM
| FREE ADMISSION EVERY DAY
manent Collection contains more than 1,000 pieces including core holdings of European and American works on paper. Academy Art Museum, 106 South Street, Easton. Tue & Wed 10 AM – 4 PM; Thurs 10 AM – 6 PM; Fri 10 AM – 7 PM; Sat & Sun 10 AM – 4 PM.

106 South Street
Easton, Maryland 21601
410.822.2787

Tiger Lily Restaurant & Tiki Bar & More Summer Events
2024-08-03 18:00 - 2024-10-26 21:30 | MD
the KG Band will be rockin’ Tiger Lily again. Come dance and listen to some of your favorite Classic Rock tunes while you enjoy the awesome Tiger Lily Tiki Bar. if you’re hungry have dinner under the shade of one of their giant umbrellas. Hope to see ya there!!
Event by The KG Band
Tiger Lily: 206 N Washington Street Easton, MD

More Events:
https://www.tigerlilyeaston.com/?fbclid=IwZXh0bgNhZW0CMTAAAR1gXDPxADwYL8Cy10kFUS8c-RmEAjQx1mcSK7o9FgmEt9Z_krIZWwmPRuw_aem_0nOgDAYyzyG402lBU4QvAQ

Books And Beer At Cult Classic Brewing Company In Stevensville
2024-08-13 18:00 - 2025-04-15 19:30 | MD
Books and Beer returns with another Blockbuster lineup of reads for 2024

This event is free and open to all who have read (You do not have to be 21).The book club discusses the book and questions about it for the first hour and spends the final 30 minutes casting it as a film/miniseries while cutting up over beverages.

Meetings are the second Tuesday of the month from 6-7:30pm*Here’s the Schedule

Feb. 13 – How Much of These Hills is Gold – C. Pam Zhang
Mar. 12 – Something Wicked This Way Comes – Ray Bradbury
Apr. 9 – The Wager: A Tale of Shiprwreck, Mutiny and Murder – David Grann
May 14 – Demon Copperhead – Barbara Kingsolver
Jun. 11 – Small Mercies – Dennis Lehane
Jul. 9 – The March – E.L. Doctorow
Aug. 13 – Jurassic Park – Michael Chrichton
Sep. 10 – History of the World in 6 Glasses – Tom Standage
Oct. 15 – Under The Whispering Door – T.J. Klune
Nov. 12 – Bad Cree – Jessica Johns
Dec. 10 – Blood Meridian – Cormac McCarthy
Check out the full Amazon wishlist here: https://www.amazon.com/hz/wishlist/ls/5163BR4WQNM7…

Kent Island Farmers Market Fall Opening
2024-09-05 15:30 - 2024-12-26 17:30 | MD
Kent Island Farmers market is in their winter hours 3:30-6:00We are a year round farmers market! All vendors accept credit cards and or online payments
POP UP VENDORS FOR THIS WEEK:

Event by Kent Island Farmers’ Market

Kent Island Farmers’ Market

OUR USUAL VENDORS:Dimitri Olive OIl: Olives, Olive oil, Infused Olive oil & Balsamics, Tapenades, Greek specialtiesCane Collective Mixers Gray Wolf DistillingCasa Carmen Winery Oksana’s Produce: Ferments, produce, Hot soupDogwood Lane Dairy: cheeses, butter, beef cutsArnaiz ChocolatGroff’s Content Farm: CHicken, Beef, Pork Lamb, freezer mealsShore Soils: Residential CompostingRefill Goodness: Great eco-conscious home and body care productsFat and Happy MicrogreensModern Stone Age Kitchen: Sourdough breads and baked goodsCafe Medrano Coffee: Organic single sourced coffeeLockbriar Produce: Apple Cider, jarred goods, honey, ice creamT’s Divine Sweets: DessertsDavis Highland Farm: Chicken EggsThe Spoiled Dog Bakery: Dog TreatsKing Mushrooms.: Gourmet mushrooms fresh, dried, tinctures & grow kits!McGlynn’s Cottage Pot PiesFern Joy LLCStem and Soul PaperArcand Wigglers: Worm Castings for fertilizing plants

Councell Farms Opening Day near Easton
2024-09-10 09:30 - 2024-10-30 17:30 | MD
Councell Farms Opening Day!

Come visit the Field of Fun, market and get our farm fresh ice cream!

Open daily 9:30-5:30 until October 30th.

Event by Councell Farms

Venue: 11773 Old Skipton Rd, Cordova, MD

September's Beer and Brushes at Ten Eyck Brewing in Queenstown
2024-09-18 18:00 - 20:30 | MD
September’s Beer and Brushes at Ten Eyck Brewing is open for registration!

We’ll be painting “Shorebird” and you’ll receive a token for your first drink. Try a new beer or grab an old favorite and the field kitchen will be available for purchasing great eats for the evening.

We’ll walk you through each element- you don’t have to be an artist or know how to draw or paint, we’ll show you all the steps and tips you need! Grab some friends and don’t wait to get your tickets, Beer and Brushes sells out quickly.

Event by Art Party Unlimited, LLC, Ten Eyck Brewing Company and Karen Saunders

Ten Eyck Brewing Company

Tickets
www.artpartyunlimited.com/service-page/september-beer-and-brushes-ten-eyck

Annual End of Summer Crab, Bull, and Oyster Roast In Grasonville
2024-09-21 10:00 - 15:30 | MD
Join us for our annual End of Summer Crab, Bull, and Oyster Roast! Enjoy crabs, oysters, pit beef, pulled pork, corn on the cob, coleslaw, domestic beer, wine, and seltzers, along with live music! Don’t miss out, as this event sells out every time

Event by Jetty Dock Bar

201 Wells Cove Rd, Grasonville, MD, United States, Maryland 21638

5th Annual EycktoberFest in Queenstown
2024-09-21 12:00 - 22:30 | MD
Join us for our 5th Annual EycktoberFest!
YOU have made this event our favorite every year!
German-inspired eats by Field Kitchen!
Games of skill including the Stein Hoist, Hammerschlagen and Beer Puppeteer!
Commemorative beer steins!
We will have the full Edelweiss Band performing 2-5PM!
It’s a full day of celebration, 12-10PM

Details

Date:
September 21
Time:

12:00 pm – 10:00 pm

Event Categories:
Local Events, Live Music, Festivals, Holiday

Organizer

Ten Eyck Brewing Company
Email:
info@teneyckbrewing.com
Website:
teneyckbrewing.com

Venue

Ten Eyck Brewing Company

205 Grange Hall Road
Queenstown, 21658 United States+ Google Map

Website:
teneyckbrewing.com

Credit: Secrets of the Eastern Shore

Dinner & Dance at the American Legion in Cambridge
2024-09-21 18:00 - 21:00 | MD
All Proceeds will be used to support our Veteran Programs!
Dinner 6:00PM – Spaghetti, Salad, Bread and Dessert.Music 7:00PM – Featuring Double Nickels!Silent Auction Table and 50/50 Raffles!
Advance Tickets are $18 or $20 at the Door.For tickets or to reserve a table, please call 410.463.1281

Event by Dorchester Post 91 American Legion

Venue: 98 Sunburst Highway, 21613

All-You-Can-Eat Seafood Extravaganza
2024-09-25 11:30 - 15:30 | MD
Date and time

Wednesday, September 25 · 11:30am – 3pm EDT

Location

Somers Cove Marina
715 Broadway Ave Crisfield, MD 21817
Show map

Refund Policy

Refunds up to 7 days before event
Eventbrite’s fee is nonrefundable.

Tickets: https://www.eventbrite.com/e/47th-annual-j-millard-tawes-crab-and-clam-bake-tickets-910605404277

Come join us for a fun-filled day of delicious seafood at Crisfield’s Somers Cove Marina. Indulge in all-you-can-eat steamed blue crabs, clams–steamed, fried or raw, corn, fried fish, fries, onion rings and watermelon! Also includes unlimited ice cold beer and soft drinks. Indulge in all of this while enjoying musical entertainment and special guests including Governor Wes Moore. This event is perfect for seafood lovers and those looking for a good time by the water–and of course some networking with politicians and organizations alike!
So, don’t miss out on this opportunity to savor some of the best seafood Maryland has to offer. Grab your friends and family and head on over to the 47th Annual J. Millard Tawes Crab and Clam Bake for a day of food, fun, and festivities!
Ticket Prices:
General Admission–$75.00
VIP Crab Trap Admission under designated “Hospitality Tent”–$110.00 (with servers)
Corporate Sponsored Tents Available (30 or more tickets). Please email office@crisfieldchamberofcommerce.com.
No Coolers Allowed In The General Admission Area.
Enjoy responsibly!

Organized by

Crisfield Chamber of Commerce

Chefs Table Seafood Night in Stevensville
2024-09-26 18:00 - 19:30 | MD
Event by Kent Island Resort

Venue: 500 Kent Manor Drive, Stevensville, MD, United States, Maryland 21666

Tickets · $103.22
www.eventbrite.com/e/chefs-table-seafood-night-tickets-942553020457

C

Join us for Chef’s Table, featuring a curated menu of the freshest seafood. Our talented chef will present an array of dishes, highlighting the flavors of the ocean.

MENU
APPETIZER
Scallop & shrimp kabob
Succotash, Roasted tomato aioli

Soup
Crab Gazpacho
Roasted heirloom tomatoes, Jumbo lump crab meat

Main Course
Pan Seared Chilean Sea bass
Jasmine Cilantro Rice, Coconut Curry, sautéed spinach,
grilled shrimp

Dessert
Exotic Cake
Mango passion mousse with mango pieces, pineapple,
bananas, lined with coconut joconde. Topped with passion fruit glaze

The Addams Family (1993) - Outdoor Movie Night at The Academy Art Museum
2024-10-04 08:00 - 22:00 | MD
They’re creepy and they’re kooky. Mysterious and spooky.
They’re all together ooky…come and see The Addams Family!
Bring a chair and a blanket for cinema under the stars! Our movie nights will be a free event for all ages.

Easton's Fall Kickoff Weekend
2024-10-04 10:00 - 2024-10-05 21:30 | MD
Event by Discover Easton
Venue: 11 S Harrison St, Easton, MD, United States, Maryland 21601
Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for a two day Fall celebration!
Website: https://discovereaston.com/fallkickoff/
Stay tuned for more details!

FRI, OCT 4th AT 4 PM to 9:45PM

Sat, OCT, 5th AT 10AM to 4PM

2 Hour Wine Tasting Cruise on Catamaran Epiphany
2026-04-15 - 2026-11-15 | Harbour Inn, 101 N Harbor Road, St Michaels MD
Your Wine Tasting Experience
Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, socializing, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully arranged seating areas, Epiphany provides the perfect setting for a relaxed and elevated wine tasting on the water.
Guests can settle into abundant cushioned seating in shaded front and rear cockpit areas, complete with dining tables ideal for wine service, or lounge at the bow in reclining captain’s chairs and comfy beanbags for a front-row view of the sails. Many guests enjoy stretching out on the trampoline, feeling the breeze, and watching the water glide beneath them while savoring each pour. Whether you’re here to unwind or explore new wines, Epiphany offers a smooth, comfortable, and engaging tasting experience.
Depart from the charming harbor of historic St. Michaels and enjoy a brief harbor cruise, including views of the 1879 Hooper Strait Lighthouse, before sailing onto the scenic Miles River. As you sail across peaceful Chesapeake Bay waters, savor a thoughtfully selected tasting of three red and three white wines, each chosen to complement the beauty and rhythm of the experience.
Your cruise blends exceptional wines with stunning waterfront views — the perfect combination for celebrations, girls’ nights, date outings, or simply gathering with friends for a uniquely memorable experience on the Bay.

Beer Tasting Cruises on Epiphany
2026-04-15 - 2026-11-15 | Harbour Inn, 101 N Harbor Road, St Michaels MD
Your Beer Tasting Experience
Step aboard Epiphany, a spacious and stable modern catamaran designed for comfort, connection, and panoramic Chesapeake Bay views. With her wide beam, open layout, and thoughtfully arranged seating areas, Epiphany provides the perfect setting for a relaxed and elevated craft beer tasting on the water.
Guests can settle into abundant cushioned seating in shaded front and rear cockpit areas, complete with dining tables ideal for tastings, or lounge at the bow in reclining captain’s chairs and comfy beanbags for a front-row view of the sails. Many guests enjoy stretching out on the trampoline, feeling the breeze, and watching the water glide beneath them while sampling each brew. Whether you’re here to unwind or explore new flavors, Epiphany offers a smooth, comfortable, and engaging tasting experience.
Depart from the charming harbor of historic St. Michaels and enjoy a brief harbor cruise, including views of the 1879 Hooper Strait Lighthouse, before sailing onto the scenic Miles River. As you glide across peaceful Chesapeake Bay waters, savor a curated selection of six craft beers featuring a variety of styles and flavor profiles, thoughtfully chosen to create a memorable tasting journey.
Your cruise blends exceptional craft beer with stunning waterfront scenery — the perfect pairing for celebrations, friends’ nights out, date outings, or simply gathering for a uniquely refreshing experience on the Bay.

Eastern Shore Sea Glass and Coastal Arts Festival
2026-04-18 - 2026-04-19 | Chesapeake Bay Maritime Museum, 213 N Talbot St, St Michaels, MD, 21663, United States
The Eastern Shore Sea Glass & Coastal Arts Festival will celebrate it’s 16th Annual Spring Edition on the beautiful waterfront campus of the Chesapeake Bay Maritime Museum in St. Michaels on April 18-19, 2026 and offers fun for the whole family with fantastic shopping, great food and drinks, live music on two stages, and more. The popular celebration of all things coastal will run Saturday April 18th 10am-5pm and Sunday April 19th 10am-4pm with all tickets valid for admission to the festival and the CBMM campus.
Tickets are on sale now at cbmm.org/SeaGlassFestival, with discounted pricing for CBMM members.
All guests save $2 by purchasing their tickets in advance online.

**There are two entrances into the festival, the Welcome Center and the entrance off Mill Street near The Crab Claw.**
This Spring Edition of the festival is set to highlight more than 100 artistans and vendors from across the country, selling an array of unique coastal and sea-glass related goods, including jewelry, home décor, art, and more. ​
While enjoying all the Eastern Shore Sea Glass & Coastal Arts Festival vendors and offerings, guests are invited to explore the exhibitions and historic structures spread across CBMM’s campus 18-acre campus. Food and beverages will be available for purchase, including craft beer and specialty cocktails.
Live music on both sides of campus will add to the celebration and festive atmosphere, with performances from local favorite musicians. The musical lineup features both returning favorites and new voices. The historic Tolchester Beach Bandstand on Navy Point will feature Chris Sacks (10am-1pm) and Jordan Sokel (1:30-5pm) on Saturday and The Uncle Ward Show (10am-1pm) and Levi Stephens (1:30-4pm) on Sunday.

The Fogg’s Landing Stage on the opposite side of campus will spotlight Dave Hawkins (10am-1pm) and Anna Burgess (1:30-5pm) on Saturday and Kenny Haddaway (10am-1pm) and Alison Thoms (1:30-4pm) on Sunday.
Throughout the weekend, guests can experience the art of glassblowing with Glass Half Full Arts. Artist Eli Cecil will lead demonstrations sharing the process of creating these one-of-a-kind artworks out of molten glass.
On Saturday, guests can sign up for a guided glassblowing experience, helping to create their own custom glass piece to take home. The cost is $100, these 30-minute sessions, which can be booked now at glasshalffullarts.com. Festival admission is included.
This program is offered with support from the Upper Shore Regional Folklife Center under the Maryland Traditions program of the Maryland State Arts Council.
Sea glass expert Mary McCarthy will be available to share her knowledge, including shard identification in the educational learning lounge, located on the Navy Point side of campus in the white building next to the Bay History #7 building, look for directional signs.
Bring your favorite finds to be identified and explore the beachcombing table.
Guests of all ages can select sea glass from McCarthy’s popular beachcombing table and use it to create a unique sea glass craft. She’ll also offer a series of films highlighting the world of sea glass available on demand in the CBMM Theater.
More family activities include a festival scavenger hunt around the campus and a mini mosaic craft with local artist Jen Wagner in the big tent on Navy Point.

While enjoying all the Eastern Shore Sea Glass & Coastal Arts Festival vendors and offerings, guests are invited to explore the exhibitions and historic structures spread across CBMM’s 18-acre campus.
Guests have a variety of ways to get out on the Miles River during the festival. We’re offering a pair of ticketed sails both days aboard 1955 skipjack Rosie Parks. Tickets for these 90-minute cruises, at 10am and noon, are $35 for CBMM members and $45 for non-members and include festival admission.
Patriot Cruises will present Narrated Historical Cruises at 12:30pm and 2:30pm on Saturday and 2:30pm on Sunday. Guests can save $10 on adult and senior tickets for all three cruises by using coupon code SEAGLASS2026 at online checkout. (Please note this discount is not to be combined with any other offer.) Combo tickets that include festival admission and the cruise are also available.
Two-day Eastern Shore Sea Glass & Coastal Arts Festival tickets can be purchased in advance online or at the door. Guests who purchase their tickets in advance will have a special opportunity to enter the festival 30 minutes early at 9:30am both days.
Ticket sales at the door begin at 10am. No single-day tickets will be sold to this rain-or-shine event.
For online sales, festival admission is set at $22 for adults, $19 for seniors (65+) and students (17+), $10 for active and retired military members, and $9 for children ages 6-to-17, with all children 5-and-younger admitted free. The cost is $2 more for all tickets for in-person sales.
CBMM members receive discounted pricing to this annual festival and others throughout the year. Adult member tickets purchased online are $10, and all children of members (17-and-younger) receive free admission.
CBMM members can also buy CBMM Festival Season Passes to make sure they’re part of all the exciting events celebrating the best of the Bay this year, including both Spring and Fall Sea Glass Festivals, Antique & Classic Boat Festival & Coastal Arts Fair, Big Band Night, Watermen’s Appreciation Day, OysterFest, and Winter on the Chesapeake. These member-exclusive passes are just $50 apiece. ​

VIP tickets include two-day festival admission with early entrance, a commemorative festival cup and discounts at the bar, a swag bag with savings at select vendors, and access to the VIP Hospitality Lounge with a complimentary beer and wine bar. The cost is $40 for CBMM members and $60 for non-members. Tickets available here

Festival tickets can be purchased in advance online or at the door. Guests who purchase their tickets in advance will have a discounted rate and a special opportunity to enter the festival 30 minutes early at 9:30am.
Ticket sales at the door begin at 10am.
During the festival, additional free event parking will be available at St. Michaels Middle/High School, with a complimentary shuttle service to and from CBMM running both days. Address for school is 200 Seymour Ave. St. Michaels, MD 21663
For safety reasons, non-service dogs need to be kept home during CBMM festivals, including the Eastern Shore Sea Glass & Coastal Arts Festival. Carry-on alcohol from dock or land is prohibited.​
​
Address for the Festival Click address for Getting Here information: 213 N Talbot St, St Michaels, MD 21663

Event is rain-or-shine.
​
We are not accepting any more vendors for the 2026 festivals, we are full. thank you.

Paint The Town Show + Sale
2026-04-25 17:30 - 20:30 | 343 High Street, Chestertown MD 21620
🎨✨ Paint the Town: Art Show & Sale ✨🎨 Get ready to celebrate creativity at Paint the Town, our exciting art show and sale featuring local artists!
Discover vibrant paintings, unique prints, and one-of-a-kind works — all available to take home and support local talent.
Whether you’re an art collector, a casual admirer, or looking for the perfect gift, this event has something for everyone. Meet the artists, explore their work, and bring a piece of your community home!
📅 Saturday, April 25th and Sunday, April 26th
📍 343 High Street, Chestertown MD 21620
⏰ April 25th starts at 5:30pm and April 26th ends at 3pm
Come celebrate art, creativity, and community — and maybe leave with a masterpiece of your own! 🖌️✨

𝐁𝐥𝐨𝐨𝐦 & 𝐁𝐫𝐮𝐧𝐜𝐡
2026-05-09 10:00 - 13:00 | Kent Island Resort
🌸 𝐁𝐥𝐨𝐨𝐦 & 𝐁𝐫𝐮𝐧𝐜𝐡🌸
𝐎𝐮𝐫 𝐌𝐨𝐭𝐡𝐞𝐫’𝐬 𝐃𝐚𝐲 𝐂𝐫𝐞𝐚𝐭𝐢𝐯𝐞 𝐁𝐫𝐮𝐧𝐜𝐡 𝐢𝐬 𝐛𝐚𝐜𝐤
If you’re looking for something meaningful (and not just another crowded restaurant brunch), this is it.
Join us at Kent Island Resort Garden Room for a creative brunch experience you’ll actually remember.
✨ You’ll create a pressed flower & butterfly resin keepsake
✨ Enjoy a delicious brunch
✨ Sip, relax, and celebrate together
✨ Plus a few special touches we’ve added just for you 👀
No experience needed — just come ready to create and enjoy time with your favorite people.
Bring your mom, your daughter, your best friend… or make it a girls day 💕
𝐖𝐡𝐞𝐧: Saturday May 9
𝐓𝐢𝐦𝐞: 10:00am – 1:00pm
𝐖𝐡𝐞𝐫𝐞: Kent Island Resort
😮Seats are limited and this event sells out every year
👉 Grab your spot now before it’s gone
https://www.facebook.com/share/18QWqA76qW/?mibextid=wwXIfr

Resin Wave Board Workshop
2026-05-13 18:30 - 20:30 | El Jefe Mexican Kitchen/Tequila Bar
Bring a touch of seaside charm into your home! In this relaxing and creative workshop, you’ll learn the art of mixing, pouring, and layering resin to create stunning ocean wave effects. With multiple board shapes and sizes to choose from, your project will be as unique as you are. These pieces make beautiful décor for your home—or thoughtful handmade gifts.
This class is beginner friendly, appropriate for ages 14 and up.
Wednesday May 13, 6:30-8:30pm
El Jefe Mexican Kitchen
1235 Shopping Center Road
Stevensville, MD 21666

Chesapeake Chamber Music Festival
2026-06-12 - 2026-06-20 | Ebenezer Theater
Where Artists, Audiences, and Acoustics Come Together in Downtown Easton, Maryland!
The Chesapeake Chamber Music Festival, now in its 41st year, is held over the course of two-weeks each June at the beautifully restored Ebenezer Theater in downtown Easton. It is a celebration of the ensembles that take on varied periods and styles of music.

Plein Air Easton (PAE)
2026-07-09 - 2026-07-19 | Waterfowl Headquarters (40 S Harrison St.)
When is Plein Air Easton?
The annual competition is held in Easton, Maryland, each July. 2026 Plein Air Easton is planned for July 10-19, 2026.
What is Plein Air Easton?
Each year, a unique juror selects 58 artists to participate. Artists apply from around the world for a chance to compete at the prestigious event. Once selected, competing artists travel to Easton to produce art from life (as opposed to in the studio) over the course of the festival.
Calendar of Events
The festival calendar features demonstrations, paint-outs, parties, and exhibitions, as well as supplementary events and local gallery demonstrations throughout the year.
Plein Air Easton (PAE) Headquarters
For one week only, Waterfowl Headquarters (40 S Harrison St.) is transformed into a central hub for all things Plein Air Easton. Whether you’re a seasoned collector or a first-time visitor, this is your must-stop destination for a dynamic, ever-evolving exhibit of plein air art—available for purchase. You’ll also find comprehensive festival information to help you make the most of your visit, free professional artist demonstrations, interviews, and engaging discussions covering a wide range of topics. JFM Frames is on site with wholesale frames, framing assistance, and supplies all week along.
20th Plein Air Easton painting frames.
No matter when you visit, PAE Headquarters offers a comfortable retreat from the summer heat. Surround yourself with fine art, watch art being created onstage during a demo, and enjoy air-conditioned comfort.

Chesapeake Film Festival
2026-10-08 - 2026-10-10 | Ebenezer Theater, Academy Art Museum, and Talbot County Free Library
Talbot County has found itself starring on the big screen from time to time, but this Oct. 8-10, 2026 the film industry becomes the star in Talbot County as it gears up for one of the most exciting cultural events of the year – the Chesapeake Film Festival.
Whether you’re a cinematic extraordinaire or just looking for a fun weekend getaway, this festival promises an unforgettable experience. Here are six sensational reasons why you should make plans to attend.
