Eastern Shore Vacation Rentals

37th Annual Christmas In St. Michaels
2023-12-08 12:00 - 2023-12-10 20:00 UTC
Christmas in St. Michaels

∴ A Weekend Celebrating Joy! ∴

Christmas in St. Michaels will be held December 8-10, 2023. We look forward to welcoming you all to our festive events throughout the weekend. Click the Events tab above to see all that we have planned.

Look forward to purchasing your favorite ornament – the new Christmas in St. Michaels Limited Edition Collectors Ornament – which will be available in late August. All proceeds from the sale of our ornaments and other products directly benefit local, non-profit organizations in our community. We invite you to join us as we welcome Santa, the spirit of Christmas, and the joy of giving.

Talbot Street Parade
2023-12-09 10:30 - 12:00 (America/New_York) | Town of St. Michaels, 101 N Harbor Rd, St.Michaels, MD, 21663, United States
Date: December 9, 2023

Time: 10:30 AM – 12:00 PM EST

Website:https://christmasinstmichaels.org/product/talbot-street-parade/

Event Description:

Who doesn’t love a traditional Christmas parade complete with marching bands, antique cars and boats, fire engines, horses, kazoo bands and llamas?! Perhaps you may even see a penny farthing. Santa and Mrs. Claus will arrive to close out the parade. Come early on Saturday morning to get a great spot along the parade route for the largest holiday parade on the Eastern Shore. Bring a lawn chair and a funny hat. Join the fun!

Berlin New Years Eve Celebrations
2023-12-31 18:00 - 2024-01-01 00:00 UTC
Celebrate New Years eve in Berlin with two ball drops. One for the kids at 6pm and the other at midnight. Laser shows, dancing and more. Free to attend and park.

Easton Carriage Tours
2024-01-12 17:00 - 2024-04-30 21:00 (America/New_York)
VALENTINE’S DAY 2024 NOW OPEN FOR BOOKINGNew this year: We are partnering with Tiger Lily for the ultimate Valentine’s experience! Have a romantic carriage ride around Easton followed by dinner ON US at Tiger Lily!
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Riding and Driving lessons can be booked by clicking BOOK NOW.
Please email Jess@Tcarriage.com or text 540-460-2455 for private rentals and driving lessons.
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We also have gift certificates available under the Book Your Tour Now option on our website for all your last minute gift needs!

Ice and Oyster Festival of Cambridge
2024-01-13 12:00 - 20:00 (America/New_York)
SCHEDULE CHANGE: Saturday, January 13th Noon-8 pm

Join us for a day of Interacting with Amazing Ice Sculptures, Eating Oysters, Live Music, and Lots of Free Family Fun

AT THE EVENT

See dazzling ice sculptures showcasing Eastern Shore culture, wildlife & more!
Entertain your family with kid-friendly golf, thrones, ice slide, and other games
Chill out in Cannery Way while feasting on local oysters and craft beer
Check out amazing Ice Bars with drinks to warm you from the inside out!
Watch top ice carvers demonstrate the artistry of their craft
Warm your hands or make a S’more at one of our fire pits
Enjoy live music on two stages throughout the event
Oyster Shucking demos

LOCATION

The Festival is in Downtown Cambridge, Maryland from Cannery Way to Blue Ruin. You can enter 411 Academy Street, Cambridge, MD into your GPS to get to the entrance of the main parking lot.

Far Eastern Shore Winery's - Sip and Stitch Sundays
2024-01-14 12:00 - 2024-03-31 16:00 (America/New_York)
About this event

Far Eastern Shore Winery invites you to join us for our Sip & Stitch Sundays series. We’ve had so much fun the past two Sip & Stitch Events over Halloween weekend and, more recently, on Small Biz Saturday, we thought we’d try to grow our stitching network.
We’ll be hosting informal crochet sessions, during which attendees can bring their own project or pick up one of our crochet kits for sale. These include a crochet hook, yarn, and a fun project with instructions.
Beginners can come to learn and practice this beloved hobby, stitch-by-stitch and crochet. Veteran crocheters can come to enjoy the company and choose to pick-up a crochet kit with beautiful yarn sourced from local yarn shop Extraordinarily Ewe, located right here in Easton, MD. You will be guided through the process step by step, or work independently, your choice!
Wine and crocheting sounds like a perfectly cozy winter Sunday in our book!

Location

Far Eastern Shore Winery
8370 Ocean Gateway Easton, MD 21601

Cost: $20

Valentines’s Cookie Class Part of the Cookie Classes collection
2024-02-04 12:00 - 13:30 (America/New_York)
About this event
Sunday, February 4 · 12 – 1:30pm EST

1 hour 30 minutes
Mobile eTicket

Valentine’s Cookie Class
Join us for a fun and delicious Valentine’s Cookie Class at Carrie Sue’s CupCakery! Get your hands dirty and learn the art of decorating cookies with our Brandy from Shore Good Cookies. This in-person event will take place at our Carrie Sue’s Cupcakery located on Main Street, Church Hill, MD, USA. Bring your loved ones or come solo, and let your creativity flow as you decorate valentines-shaped cookies with sweet icing and colorful sprinkles. Ticket includes a glass of wine for those over 21 and complimentary snacks courtesy of Carrie Sue’s Cupcakery! Whether you’re a baking enthusiast or just looking for a fun activity, this class is perfect for all skill levels. Don’t miss this opportunity to create scrumptious treats and make lasting memories. Book your spot now!

General Admission

$45.00

Carrie Sue’s CupCakery, Main Street, Church Hill, MD, USA
512 Main Street Church Hill, MD 21623

Pirate & Mermaid Valentine Brunch
2024-02-10 11:00 - 13:00 (America/New_York)
About this event

2 hours
Mobile eTicket
$15-20 per ticket

What better way to celebrate Valentine’s weekend than spending it with the little ones that you love. Join us for a fun morning filled with great food, fun crafts, family-friendly games, and more.

Date and time

Saturday, February 10 · 11am – 1pm EST

Location

959 Baltimore Annapolis Blvd
959 Baltimore Annapolis Boulevard Severna Park, MD 21146

Endless Vision’s Valentines Gala
2024-02-10 18:00 - 23:30 (America/New_York)
About this event

5 hours 30 minutes
Mobile eTicket
$50-75 per ticket

come out and enjoy yourselves with some live music good vides with a prom theme and setting with a red carpet that meets you to your car with a photographer waiting to flick you up as well as proformances by Ms Ayla Dennis and food by Tahya Jones and Tynell Copper and Helen And Rae’s and Dj Vibes on the ones and twos.

40 S Harrison St
40 South Harrison Street Easton, MD 21601

411 kitchen winter dining experience
2024-02-10 19:30 - 21:30 (America/New_York)
Join us for an unforgettable dining experience at Layton’s Chance Vineyard & Winery. Indulge in a delectable culinary journey prepared by our talented chef Chris, showcasing the finest ingredients and flavors. Immerse yourself in the cozy ambiance of the vineyard, surrounded by breathtaking views and the soothing sounds of nature. Savor each bite as you sip on exquisite wines of Layton’s Chance Vineyard & Winery, perfectly paired to elevate your dining experience. Whether you’re a food enthusiast or simply looking for a memorable night out, this event promises to delight your taste buds and create lasting memories. Don’t miss out on this extraordinary opportunity to indulge in a truly unique dining experience.
**Wine Pairing Ticket and additional beverages are available separately at the bar.
**For details on Corporate Sponsorships, email us at info@411.kitchen or check out our website at https://411.kitchen.

Event Categories:
Home Page Featured, Layton’s Chance

Venue

Layton’s Chance Vineyard & Winery

4225 New Bridge Rd
Vienna, MD 21869 United States+ Google Map

Phone:
410-228-1205

Chesapeake Fire & Ice of Easton
2024-02-16 17:00 - 2024-02-17 21:00 (America/New_York)
Chesapeake Fire & Ice Festival Returns to Easton, MD in 2024!
Larger-than-life sculptures made of solid ice will be on display throughout the historic downtown!
Festival will feature dozens of ice sculptures throughout Easton’s Historic District. Friday nights kick off will feature live ice carvings, music, and restaurant specials. The celebration will offer free live music and fire performances, outdoor ice skating, and the unveiling of the weekend’s ice sculptures with a free self=guided tour and light display
Stay tuned for more updates!

DOWNTOWN EASTON, MD

Cars and Coffee in the Barn Classic Motor Museum Saturdays
2024-03-02 09:00 - 2024-05-04 16:00 (America/New_York) | Motor Museum, 102 E. Marengo Street, St. Michaels, MD, 21663, United States
Hosted by: Classic Motor Museum St Michaels
Where: 102 E. Marengo Street, St. Michaels Maryland.
When: Every Saturday Morning 9 am to 11 am.
From now through the end of March we have a “Coffee in the Barn” event every Saturday.
This happens directly in the museum barn. It is free for members and $5 for non-members.
It is from 9 am to 11 am.
Starting in April we go back to our outdoor event “Cars and Coffee” which is free to everyone and open for others to bring their classic cars and show them on our campus.
Regular Winter Hours for the Museum:
Open every Friday and Sunday from 11 am to 3 pm, Saturday open from 9 am to 4 pm.
The cost is $10 per person.

Build-Your-Own Bloody Mary/Maria Bar at The Fool's Lantern
2024-03-02 10:00 - 2024-04-28 14:00 (America/New_York) | The Fool’s Lantern, 310 S. Talbot St., St.Michaels, MD, 21663, United States
Join us every Saturday and Sunday at The Fool’s Lantern for brunch and our Build-Your-Own Bloody Mary/Maria Bar! Choose from a variety of vodka or tequila, add our house made mix, and then choose from over 20 toppings to create your unique drink. Pair it with items from our brunch menu to start your weekends off right!

6th Annual St. Michaels ChocolateFest
2024-03-02 11:00 - 16:30 (America/New_York) | Town of St. Michaels, 101 N Harbor Rd, St.Michaels, MD, 21663, United States
St. Michaels ChocolateFest will be held March 2, 2024 and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts. The Chocolate Crawl will take place on Saturday, March 2, 2024 from 11:00 a.m. – 4:00 p.m. until sold out throughout the Town of St. Michaels at participating businesses and restaurants. There will be no tickets sold in advance, so come hungry and bring cash to pay for delectable items throughout the Town of St. Michaels.
Chocolate lovers will enjoy shopping throughout town sampling amazing artisan chocolates, desserts, wine, beer and spirits.

Purchase tasting samples directly from participating Tasting Venues.
Restaurants will have other chocolate items to purchase as well as many shops will have chocolate items for purchase!
CRAWL TIPS:
Come hungry!
Bring $1 and $5 dollar bills
Bring family and friends to enjoy together
Wear comfy shoes

The ChocolateFest Crawl is a rain or shine event.

Simpatico Free Wine Tasting Events Every Weekend
2024-03-02 12:30 - 2024-04-28 16:30 (America/New_York) | Simpatico, 104-106 Railroad Ave, St.Michaels, MD, 21663, United States
top by Simpatico’s Courtyard or in the Shop at 104-106 Railroad Ave, just off Talbot Street, every weekend for free tastings of our hand-picked Italian wines! Peruse the shop and chat with our enthusiastic staff – We Love All Things Italian! We also offer free tastings all week long. Salute!

2nd Annual Peake Irish Experience for Annapolis St Patrick's Day
2024-03-09 12:00 - 18:00 (America/New_York)
About this Event

Get ready for our second St. Patrick’s Day bar celebration with authentic Irish beverages for the biggest Irish holiday! Introducing The Peake Irish Experience, an Irish bar journey brought to you by Peake Social, Guinness, Emerald Society of Firefighters, and in partnership with Shamrock the Dock!
Join us as we make our way down the streets of Annapolis, visiting some of Naptown’s most popular bars and pubs featuring Irish drink and food specials.
Each attendee will receive Irish giveaways, door prize chances, drink specials, and live entertainment! Additionally, add on a special priced ticket to Shamrock the Dock festival happening on Ego Alley on March 16th and 17th!
The 2nd Annual Peake Irish Experience will kick off at 12 pm on March 9th, 2024 with the first 25 to arrive receiving a complimentary Guinness at the first stop. Along the way, participants will receive drink specials and have the chance to win prizes from our sponsors, including gift cards to participating bars and a grand prize of an Open Gate Brewery tour and gift card.

Spring Vendor Market In Cambridge
2024-03-12 08:00 - 17:00 (America/New_York)
Join on April 6th from 9am- 1pm
Lots of vendors including Scentsy, tastefully simple, thirty one, Tupperware, paintings, jewelry, tumblers, wreaths, leather goods, signs, cupcakes, country decor, handmade items, candles, bath salts and lots more. The Auxiliary will also be serving breakfast and lunch during the Event. Hope to see you there. Please come out and support our amazing vendors and The American Legion Auxiliary Unit 91
Venue:
Dorchester Post 91 American Legion
Organizer:
https://www.facebook.com/events/1369025347827240/

St. Patrick’s Day Celebration Dinner in Oxford
2024-03-14 18:00 - 20:00 (America/New_York) | Oxford Community Center, 200 Oxford Road, Oxford, MD, 21654, United States
Traditional Irish dinner:
MARCH 14 @ 6:00 PM
Corn beef, Cabbage, Potatoes and Irish Soda bread (prepared by a team of OCC chefs)

$25/person (with cash bar)
Live Music
Reservations by March 8

Dine In or Carry Out
VENUE

Oxford Community Center

200 Oxford Road
Oxford, MD 21654 United States + Google Map

Phone
410-226-5904

View Venue Website

Opening day at Scottish Highland Creamery
2024-03-15 15:00 - 20:00 (America/New_York)
Opening day at Scottish Highland Creamery from 3:00 pm to 8:00 pm. Face painting 3:00 – 5:00, new ice cream flavors, special prize for 1st customer of the season!
DETAILS

Date:
March 15
Time:

3:00 pm – 8:00 pm

VENUE

Scottish Highland Creamery

314 Tilghman St
Oxford, MD 21654 United States + Google Map

Phone
410-924-6298

St. Pat's Karaoke Night @ Lil' Bitta Bull
2024-03-15 21:00 - 23:30 (America/New_York)
Join Leprechaun Lucky Chuckie as we kick off St. Patrick’s weekend! Friday Night Karaoke starts at 9 p.m. at Lil’ Bitta Bull BBQ and going until…
$5 Lucky Shots all night!
Kitchen is open til 9 pm, come for dinner, stay for the show!

Date and Time
Friday Mar 15, 2024
9:00 PM – 11:55 PM EDT

Location
Lil’ Bitta Bull BBQ
520 Race Street
Cambridge, MD 21613

Website
https://www.facebook.com/lilbittabull

Contact Information
443-205-2219
Send Email

20th Annual Eagle Festival
2024-03-16 09:00 - 16:30 (America/New_York)
The 20th Annual Eagle Festival at Blackwater National Wildlife Refuge on Saturday, March 16, 2024, from 9:00 a.m. to 4:00 p.m. as we celebrate birds of prey! Don’t miss out on this free event for the whole family, with live raptor programs, kids’ activities, refuge tours, exhibits, and more! Call 410-228-2677 for more information or visit us online at www.fws.gov/refuge/Blackwater.
Blackwater National Wildlife Refuge, located on the Eastern Shore of Maryland, protects over 32,000 acres of rich tidal marsh, mixed hardwood and pine forest, managed freshwater wetlands and cropland for a diversity of wildlife. To learn more, visit our website at http://www.fws.gov/refuge/blackwater or @BlackwaterNWR.
The mission of the U.S. Fish and Wildlife Service is working with others to conserve, protect and enhance fish, wildlife, plants and their habitats for the continuing benefit of the American people. We are both a leader and trusted partner in fish and wildlife conservation, known for our scientific excellence, stewardship of lands and natural resources, dedicated professionals and commitment to public service. For more information on our work and the people who make it happen, visit http://www.fws.gov.
U.S. Fish & Wildlife Service
Date and Time

Saturday Mar 16, 2024
9:00 AM – 4:00 PM EDT

Location
Blackwater National Wildlife Refuge
2145 Key Wallace Drive
Cambridge, MD 21613

Website
http://www.fws.gov/refuge/Blackwater

Contact Information
410-228-2677
Send Email

Candle Light Cove's Spring Festival
2024-03-16 10:00 - 13:00 (America/New_York) | Candle Light Cove, 106 W Earle Ave, Easton, MD, 21601, United States
About the eventCandle Light Cove’s Spring Festival
Open to the public! Free event! Community partner festival/yard sale, shop from local vendors, Easter Bunny, Food Trucks, Peep Show Voting & Winners Announced!

Cambridge Rotary Community Foundation Oyster Festival
2024-03-16 12:00 - 16:00 (America/New_York)
Join us for a shuckin’ good time at the Cambridge Rotary Community Foundation Oyster Roast!
Indulge in delicious oysters, mingle with fellow oyster enthusiasts, and support a great community organization. This in-person event promises to be a shell of a good time. Don’t miss out!
In addition to oysters, we will have hamburgers and hot dogs. Drinks options will include water, soda, beer, wine, and orange crushes.
Live music from Anna Burgess.
$5 donation per person to attend the event. $1 tickets will be sold to use as currency for food and drinks once in the building. If you pre-purchase tickets, you will get extra: Purchase 100 and get 110 tickets, purchase 50 and get 5 tickets.
Tickets will be sold at the door for $1 each.
Oysters – 1 ticket each (raw or scalded)
Hot dog – 2 tickets
Hamburger – 3 tickets
Water & Soda – 1 ticket
Beer & Wine – 5 tickets
Crushes – 8 tickets
Click Here for Tickets

Date and Time
Saturday Mar 16, 2024
12:00 PM – 4:00 PM EDT

Location
Minnette Dick Hall
2000 Hambrooks Blvd
Cambridge, MD

Website
https://www.eventbrite.com/e/cambridge-rotary-community-foundation-oyster-festival-tickets-851521442557?aff=ebdssbdestsearch

St. Patrick's Day Karaoke at Old Salty's Restaurant
2024-03-16 19:00 - 23:00 (America/New_York)
Chuckie Hayward will be at Old Salty’s Restaurant celebrating St. Patrick’s day with karaoke! Stay tuned for drink and food specials to be posted on their Facebook Page.

Date and Time
Saturday Mar 16, 2024
7:00 PM – 11:00 PM EDT

Location
Old Salty’s Restaurant
2560 Hoopers Island Road
Fishing Creek, MD 21634

Website
http://ww.oldsaltys.com

Contact Information
410-397-3752
Send Email

RAR Brew & Irish Stew St. Day The Local Way In Cambridge
2024-03-17 08:00 - 17:00 (America/New_York)
Introducing a pop up event you won’t want to miss-our RAR BREW & IRISH STEW DRIVE THRU!!!!!
RAR has sent over some of their Leprechaun Bait Out of Order cans (maybe the most popular can of the season) and we’re ready to pair it with some HOMEMADE Irish beef stew cooked up the Emily’s way!!!
We’ll also have some Scottish Highland quarts, a few other baked good selections, and our food truck will be serving up some “better than gold” goodies!!
Make sure to place your order on our online store for pickup on March 17th (we have a feeling that the RAR brew will go quick) and get ready to do a little Irish jig with us
ORDER HERE: emilysproduceorders.com
See less

Organizer:
Event by Emily’s Produce

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

Easton's St. Patrick's Day Parade
2024-03-17 09:00 - 11:30 (America/New_York) | 106 W Dover st, 106 W Dover St, easton, MD, 21601, United States
Join Talbot Thrive for St. Patrick’s Day!
As St. Patrick’s Day approaches, we’re gearing up for an exciting celebration in Easton, and we want YOU to be a part of it! This year, we’re organizing a unique and inclusive contingent for the parade – one that’s vehicle-free and full of energy. Whether you’re a seasoned cyclist, a skilled skateboarder, or someone who uses a wheelchair, there’s a spot for you at the St. Patrick’s Day Shamrock and Roll on March 17!
Joining our contingent means not only celebrating Irish culture and heritage, but also aligning with the mission of Talbot Thrive. This year’s vehicle-free parade emphasizes sustainable and eco-friendly modes of transportation, which perfectly reflects Talbot Thrive’s commitment to environmental stewardship and community wellness. It’s a fantastic opportunity to showcase your talents, enjoy the festive atmosphere, and promote a greener, more accessible future for all.
Please sign up so we know you’re coming! https://form.jotform.com/240226017614143

Adult Easter Egg Hunt 2024
2024-03-22 18:00 - 21:00 (America/New_York)
Join in the fun at Layton’s Chance!
This adult only Easter Egg hunt is a twist on the traditional hunt!
At 6:00pm blindfolded teams of 2 will compete during fun and goofy ways to find hidden eggs. Entertainment, prizes, and of course lots of laughs will fill this evening!
After the hunt there will be music, additional games and more prizes to win! Registered team check-in opens at 5:30pm.
Blindfolded Egg Hunt and Party Admission for 2 people ~ $48/team of 2
If you would like to register for the party (no hunt) admission, click here!
Over 21 only, sprinkles or shine.
Food and nonalcoholic drinks may be brought to the winery,
but no other alcohol is allowed on the property per Maryland law – coolers will be checked.
Tickets are non-refundable Register Now!

Date and Time
Friday Mar 22, 2024
6:00 PM – 9:00 PM EDT

Location
Layton’s Chance Vineyard & Winery
4225 New Bridge Road
Vienna, MD 21869

Website
http://www.laytonschance.com

Contact Information
410-228-1205
Send Email

3rd Annual Glow In The Dark Easter egg hunt At The Queenstown's Moose Lodge
2024-03-22 20:00 - 21:00 (America/New_York)
Friday night, March 22nd for our 3rd Annual Moose Glow in the Dark Easter Egg Hunt!
There’s nothing else that will make you feel like a kid again then hunting Glow in the dark eggs filled with treats!!

$15/person to participate, you’ll find eggs filled with scratch offs, liquor minis, moose bucks, drink chips and more!!

Bring a flash light if you like….or a friend! Open to Members and Qualified Guests!!

"Hello Spring" Annual Spring Celebration In Stevensville
2024-03-23 10:00 - 16:00 (America/New_York)
Annual Spring Celebration!! Come celebrate sunshine and flowers! We have the sweetest little free gift (with purchase) for you along with sweet treats, tasty drinks and lots of other specials.
We will be donating 10% of our sales this day to our new neighbor and nonprofit, Ebeauty. Ebeauty’s mission is to improve the quality of life of women going through chemotherapy through their wig exchange program. You will get the chance to meet the amazing women behind this special organization, as well!
Date:
March 23rd from 10am – 4pm
Venue:
480 Main Street, Suite 100, Stevensville, MD, United States, Maryland 21666
Organizer:
Event by Half Full

Awww Shucks Oyster Harvest In Queenstown
2024-03-23 13:00 - 17:00 (America/New_York)
They will be shucking oysters all day long! More details as we get closer to the day.
What pairs better with a briny, sweet oyster than an ice cold fresh beer?
Date:
March, 23rd @ 1pm

Venue:
205 Grange Hall Road, Queenstown, MD, United States, Maryland 21658

Organizer:

Event by Ten Eyck Brewing Company and Field Kitchen
