Eastern Shore Vacation Rentals

Chesapeake Film Festival
2023-09-30 19:00 - 21:00 UTC
Save the dates! The 2023 Chesapeake Film Festival (CFF) will be LIVE Sept. 30 and Oct. 1 at two historic venues in Easton, MD. The Festival goes VIRTUAL October 2 through 8, bringing you more fabulous films to watch anytime, anywhere.
The hybrid festival begins with a LIVE weekend (Sept. 30 and Oct. 1) featuring screenings, discussions, events at the Avalon Theatre and Ebenezer Theatre, as well as an Opening Day VIP Reception at the Academy Art Museum. As viewers take their seats in these beautifully restored venues, they are transported into the glory days of theatre.
The VIRTUAL Festival (Oct. 2-8), which follows the LIVE Festival, gives film lovers another week of outstanding films to watch at their convenience. Viewers can view films from a variety of genres including narratives, documentaries, and animations. Take five minutes to watch a pithy short film or grab some popcorn and treat yourself to a fabulous full-length feature.

Maryland Folk Festival
2023-09-22 18:00 - 2023-09-24 21:00
Make your plans now to join us in Salisbury, Maryland, for the Maryland Folk Festival— a diverse celebration of arts, culture, and heritage.
This large-scale multi-day outdoor event, celebrates the roots, richness and variety of American culture. It features hundreds of the nation’s finest musicians, dancers, craftspeople and other keepers of culture in performances, workshops, and demonstrations, plus children’s activities, non-stop participatory dancing, storytelling, parades, and more.
Best of all, it’s FREE!

Crab Feast in Annapolis
2023-09-17 14:00 - 18:00
Crab Feast 2023 is finally here! Join us on Sun Sep 17, 2023 at 2 Pythian Drive Edgewater, MD 21037 for a day of fun, food, and festivities. This in-person event is perfect for all crab lovers out there. Get ready to indulge in the freshest and most delicious crabs you’ve ever tasted!
Our event will start at 2:00 PM Eastern Daylight Time. Come early to avoid the lines and get the best seat in the house. We will have food, music, games and fun. You won’t want to miss out!
Aside from the mouth-watering crabs, there will also be a selection of other dishes available, as well as refreshing drinks to keep you cool throughout the day. Fried chicken, hot dogs, pasta, Maryland crab soup, coleslaw, potato salad, assorted desserts, domestic bottled beer, house wines, sodas, lemonade, coffee, and iced tea. *Open Bar Available*
Bring your friends and family along for a day of bonding over delicious food and good vibes.
Don’t forget to bring your appetite and your dancing shoes! We can’t wait to see you at Crab Feast 2023!

Murder Mystery Dinner Cruise (September 16th)
2023-09-16 18:00 - 21:00
Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore!
The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river.
Catered by Suicide Bridge Restaurant and features local seafood and Eastern Shore favorites including Dinner Choice of one Prime Rib and Crab Cake or (2) Lemon Chicken and Crab Cake
Dinner Side: Potato of the Day, Green Vegetable
Dessert
Non-Alcoholic Beverage

Wine Down at Laytons Chance Winery
2023-09-16 16:30 - 20:30
It’s that time of year!!! Zeta Phi Beta Sorority, Incorporated, Iota Chi Zeta Chapter will host it’s annual “Wine Down”. This fun for all event will be held on Saturday, September 16, 2023 at Layton’s Chance Vineyard from 4:30-8:00 pm. Tickets are $45 (until July 1st) which includes wine tasting, food, and entertainment. After July 1st, tickets are $50. Late tickets will be sold if there are still tickets available.
This is a rain or shine event. A portion of the proceeds will benefit community outreach programs and our various scholarship programs.
We will have jewelry and Greek apparel vendors. Guests are encouraged to bring lawn chairs to enjoy the entertainment. Please obey all parking instructions to preserve the beauty of the winery. We will have vendors. Parking is free.

The Maryland Wine Festival of Carroll County
2023-09-16 11:00 - 17:00
Carroll County’s 39th Maryland Wine Celebration!
An Outdoor Event Featuring Wine, Live Music, and Local Vendors.

Explorer Pass | $65*

Enjoy an upgraded Maryland Wine Festival experience. The Explorer Pass includes admission to the Main Field, the Maryland Wine Explorer Village and includes:
• Exclusive, curated Maryland-grown wine samples
• Admission to an exclusive seating area *
• Complimentary filtered water *
• Private, air-conditioned restroom facilities
• Access to the Maryland Wine Shop
* Be sure to bring a refillable water bottle and keep hydrated throughout your day at the Maryland Wine Festival! While some picnic tables will be provided, guests should bring chairs and blankets for the Explorer Village.

General Admission | $30*

Enjoy the Maryland Wine Festival from the Main Field. General Tasting Passes include:
• Sample wines in the Main Field
• Access to the Maryland Wine Shop
• Souvenir tasting glass
* THIS PASS DOES NOT ALLOW ENTRY TO THE MARYLAND WINE EXPLORER VILLAGE.

Artisans on the Choptank
2023-09-16 08:00 - 2023-12-02 17:00
Artisan Market featuring local artisans! We will have a DIY craft, flower bar, craft beer, food and music! No cost to attend!
Rain or shine- we will set up outside weather permitting. This is two events in 2023!

September 16: 11am-3pm

December 2nd: 4pm-10pm

IRONMAN MARYLAND
2023-09-16
At IRONMAN Maryland, part of the VinFast IRONMAN North America Series, race day does not make us individuals that are competing against ourselves. When we toe the line, we become a team of athletes that join forces to overcome whatever challenges race day brings. We are allies that stick by each other and offer words of encouragement. And most of all, we are a community of finishers who are grateful to experience the camaraderie of Crabby Nation year after year.
We are Crabbies and this is Crabby Nation.
Embrace the journey to becoming an IRONMAN. Embrace the journey to becoming a Crabby.

Feasting Over Fire Series with Chesapeake Chefs
2023-09-13 18:00 - 2023-10-13 20:00
Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more.
Reserve Your Seat at the Table: Feasting Over Fire Dinner Series with Chesapeake Chef Service at Brampton Inn
Experience a quintessential Eastern Shore tradition and join us at Brampton Inn for an open-fire cauldron dinner that is a love letter to what’s in season. Chef Kurt Peter and his talented team from Chesapeake Chef Service is firing up the flame to create an imaginative, robust menu to celebrate the diverse seasonal abundance of local farmers, watermen, cheesemakers, vintners, and brewers to highlight the subtle changes of flavor throughout the season.
Set on the scenic alfresco Renaissance Garden terrace, each Feasting Over Fire menu will change and includes:
• Begin your visit with seasonal appetizers and craft cocktails garnished with herbs straight from the Brampton’s lush garden.
• Gather around a communal table to savor a decadent multi-course dinner by Chef Peter showcasing the finest local ingredients from neighboring farmers and watermen, paired with remarkable wines or spirits chosen by Chef Peter.
• Throughout the evening we will be entertained by the musical stylings of concert pianist, Michael Casey, who hails from Rock Hall.
• $120.00 per person includes gratuity. No fees.
• Available September 13th and October 12th, 6pm – 8pm. Dinner themes and menus will be forthcoming.
• Advance ticket purchase required. No walk-ups accepted. Ticket sales end 2 days prior to the event.
Extend your experience by making reservations to stay at Brampton Inn. Book online at https://bramptoninn.com/ or call 410-778-1860. Guests of the Inn will enjoy a bottle of Champagne and can retire to one of the many cozy seating areas, fire pit or the comfort of their cottage or suite and continue in their enjoyment of the enchanting evening. A decadent breakfast is included each morning of your stay.

Light Night at Cambridge Yacht Club
2023-09-09 18:00 - 22:00
The annual LIGHT NIGHT is Saturday, September 9, 2023, at the Cambridge Yacht Club.
A celebration of the Choptank River Lighthouse and the difference “The Jewel of the Choptank” is making for our community, the event will feature heavy appetizers, fun auctions, a “wine wall,” dancing, and much more.
Outdoor tented space available in addition to air-conditioned Yacht Club interior.
Indoor and outdoor bar will be open for drink purchases.
Live and Silent auctions.
Tickets cost $75. The event has sold out every year, so order early!
Proceeds benefit the Cambridge Lighthouse Foundation, a 501(c)3 nonprofit whose mission is to promote visitation to the Lighthouse and enhance the experience of visitors. More than 25,000 people have visited the Lighthouse since it opened. The beacon has become a powerful symbol for the revitalization of Cambridge and Dorchester County.

Easton Music Bingo at Doc's Downtown Grille
2023-09-07 19:00 - 2024-03-07 21:00
MUSIC BINGO – Free to play, Prizes to win! No ticket required, first-come, first-served. Possession of a ticket does not guarantee a seat at the gameshow. Contact the venue to discuss best time to arrive to get a seat.
Play That Funky Bingo is like regular bingo but instead of calling numbers, we play parts of songs. If the song is on your card, dab it! Get 5 in a row, FUNKY BINGO! 7 Bingo Winners EACH ROUND!
Music genres are diverse, from Pop to Country, Classic Rock to Motown, Disco to New Wave.
DON’T WORRY! This isn’t trivia! Your host will announce song titles after anyone in the audience identifies the song or if time runs out. (That almost never happens.)
We will be playing using REAL BINGO DABBERS and BIG letter-sized Bingo Cards, so no squinting required.
Or, if you prefer you can use our app for CONTACT FREE PLAY! For Covid safety, your card will appear on your smart device such as a smart phone, tablet, iPad, Chromebook, etc. It’s SUPER EASY TO PLAY!
NIGHTLY PRIZES

Avalon Theater Jazz Experience Aug 3rd
2023-09-02 15:00 - 18:00
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre!
SUN
9/3
3:00pm-6:00pm

AVALON JAZZ EXPERIENCE
ALLAN HARRIS: KATE’S KITCHEN

The Avalon Theatre invites you and your friends to enjoy the unofficial end of the summer in Easton with the soulful and swinging sounds of Jazz. This premier event will captivate music lovers and jazz enthusiasts alike and the Avalon Staff is extremely excited about this year’s line-up!

Tier 1
$62.00 (inc. $2.00 service charge)*

Tier 2
$52.00 (inc. $2.00 service charge)*

Tier 3
$42.00 (inc. $2.00 service charge)*

Avalon Theater Jazz Experience Aug 1st
2023-09-01 20:00 - 22:00
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre!
Date
September 1, 2023 8:00 pm – 10:00 pm
Sammy Miller and the Congregation: The Music of 1973

The Avalon Theatre invites you and your friends to enjoy the unofficial end of the summer in Easton with the soulful and swinging sounds of Jazz. This premier event will captivate music lovers and jazz enthusiasts alike and the Avalon Staff is extremely excited about this year’s line-up!

Tier 1
$62.00 (inc. $2.00 service charge)*

Tier 2
$52.00 (inc. $2.00 service charge)*

Tier 3
$42.00 (inc. $2.00 service charge)*

First Fridays at Hunters Tavern
2023-09-01 15:30 - 18:30
Hunters Tavern will be doing a special $5 first Friday all summer long starting June 3rd!
With $5 drafts, $5 glasses of house wine, $5 flatbread, and more, your Fridays just got much better!

Murder Mystery Dinner Cruise (August 19th)
2023-08-19 18:00 - 21:00

Avalon Theater Jazz Experience Aug 2nd
2023-08-09 20:00 - 22:00
Make your plans now for Labor Day Weekend and the Jazz Experience at The Avalon Theatre!

The Avalon Theatre invites you and your friends to enjoy the unofficial end of the summer in Easton with the soulful and swinging sounds of Jazz. This premier event will captivate music lovers and jazz enthusiasts alike and the Avalon Staff is extremely excited about this year’s line-up!

SAT
9/2
8pm-10pm

DOMINICK FARINACCI AND FRIENDS

Tier 1
$72.00 (inc. $2.00 service charge)*

Tier 2
$62.00 (inc. $2.00 service charge)*

Tier 3
$52.00 (inc. $2.00 service charge)*

Dinner Under The Stars
2023-08-09 17:00 - 2023-09-23 22:00
Enjoy outdoor dining and music on Wednesday and Saturday evenings 5pm-10pm May 20th-September 23rd on Inner West Street in Annapolis. The streets are filled with café tables, live music and dancing. Reservations are encouraged.

The 9th Annual Sudlersville Peach Festival 23'
2023-08-04 18:00 - 2023-08-05 16:00
Friday, August 4 6PM until Fireworks

Saturday, August 5 10AM – 4PM

Sudlersville Peach Festival is co-hosted by the Sudlersville Volunteer Fire Company. With the best local bands providing live music, community non-profit groups serving great homemade food from pit beef to peach cobbler, local vendors offering their best hand-made crafts, and lots of great family activities, this event is a true community gala that promises to be a great time for the whole family.

There is no admission fee or tickets to attend this event. Free onsite parking available directly behind the farm market.

The 78th Annual Annapolis Crab Feast
2023-08-04 17:00 - 20:00
Held rain or shine since 1946, the Annual Rotary Crab Feast is one of the longest-running and most popular summertime traditions in Annapolis!
Known as “the world’s largest crab feast,” the all-you-can-eat (and drink) event invites folks from near and far to get their fill of Maryland’s famous blue crabs – plus Maryland vegetable crab soup, sweet Maryland corn on the cob, beef barbeque sandwiches, all-American hot dogs, watermelon, draft beer, and assorted sodas and water – at Navy-Marine Corps Memorial Stadium each August.
Crab Feast Tickets & Raffle Tickets will go on sale soon!

U.S. Navy Band Cruisers Summer Outdoor Concert Series
2023-07-29 19:00 - 21:00
The Avalon Summer Outdoor Concert Series is located on Harrison Street between Dover and Goldsborough Streets, begin at 7pm. They are free and open to the public. Bring some chairs and prepare to enjoy a pleasant evening of musical fun with your friends and family or call Hunters Tavern to make a dinner reservation on the patio Children are welcome and dancing is encouraged. Rain venue: Avalon Theater. The U.S. Navy Band Cruisers play pop and rock style music.

Thunder on the Choptank Boat Races
2023-07-22 11:00 - 2023-07-23 17:00
Thunder on the Choptank Boat Races at Gerry Boyle Park at Great Marsh.

Sail on the Skipjack Nathan (July 22nd)
2023-07-22 10:00 - 12:00
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew.
Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per trip and the boat leaves the dock promptly on schedule.
Booking – Skipjack Nathan (skipjack-nathan.org)

Adults
Children Aged 4–12
Children Under Age 4

$40.00
$15.00
Free

Murder Mystery Dinner Cruise (July 15th)
2023-07-15 18:00 - 21:00

Saucy by the Shore Festival 2023
2023-07-15 12:00 - 18:00
FELLOW SAUCE LOVERS!

Join us for a Deliciously Epic Adventure.
Taste Bud Exploding Local & National Sauce Companies! Varieties of Award-Winning Savory, Sweet, Hot, Tangy & more! FIND YOUR FLAVOR: Free Samples from Most Attending Sauce Vendors. Several Hot Sauces have been featured on the Hit YouTube series: Hot Ones!
​AWESOME LIVE MUSIC ON STAGE, YUMMY FOOD VENDORS, TASTY BEVERAGES, ​MOBILE RAGE ROOM, OUTDOOR AXE THROWING, WING EATING CONTEST, FAMILY ADVENTURES
TICKET OPTIONS

ADULT ADMISSION:
$20 ADV. / $25 DAY OF* ADULT SQUAD PACK: 5 FOR THE PRICE OF 4!
KIDS AGES 6 – 12:
$10 ADV. / $15 DAY OF
KIDS 5 & UNDER ARE FREE!
​
EXTRA SAUCY PACK: $50INCLUDES* Cool Misted VIP Tent with Private Bar
* 11am Early Admission* Separate Entry Line* Air Conditioned Private Restrooms
• Parking Spot* Commemorative Tote Bag* 16oz Commemorative Cup• Sauce Roulette: One Bottle of Random Hot Sauce* One Drink Ticket

Sail on the Skipjack Nathan (July 15th)
2023-07-15 10:00 - 12:00

Summer Music at Blue Ruin Cocktail Bar & Restaurant
2023-07-14 20:00 - 2023-08-26 22:00
Offers small plates with intense flavors and specializes in over 150 different kinds of cocktails!
Join Blue Ruin for live music on these dates!
July 14th – Bryan Russo 8-10pm
July 21st – Jayme Dingler 8-10pm
July 22nd – Garrett Roe Karaoke 7-10pm
July 28th – Alli Pinsky 8-10pm
July 29th – Sam Pugh 7-10pm
August 5th – Joe Hickey 7-10pm
August 11th – Bryan Russo 8-10pm
August 12th – Garrett Roe Karaoke 7-10pm
August 18th – Alli Pinsky 8-10pm
August 25th – Jayme Dingler 8-10pm
August 26th – Sam Pugh 7-10pm

A couple a new recommended cocktails to try!
Twist My Arm
Titos Vodka, Armagnac, Pineapple, Lemon Juice, Honey
​McCoy’s Negroni
Real McCoy 12yr Rum, Cappelletti, Sweet Vermouth
​Down The Rabbit Hole
Banhez Mezcal, Agave, Cranberry, Lime Juice, Empress Gin Floater
​

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Plein Air Easton
2023-07-14 - 2023-07-23
Plein Air Easton is the largest outdoor art competition in the nation and is celebrating its 19th year in 2023. Competition artists who have been juried in will descend on Easton to have their canvas’ officially stamped on July 13th. Public, ticketed and free events (for the kids too) take place all week long beginning with the ‘Welcome Plein Air Easton Block Party and Nocturne Paint-out’ throughout downtown Easton on July 14th.

Wine & Unwind with Local Artists at Layton's Chance
2023-07-09 13:00 - 2023-08-19 17:30
Wine & Unwind with Marianna Styles
Sunday, July 9, 2023 from 1:00 PM to 4:00 PM EDT
Sip wine, enjoy live music by Marianna Styles No fee, no reservation.
Layton’s Chance Vineyard & Winery

Summer Concert with Uprizing
Saturday, July 22, 2023 from 6:00 PM to 9:00 PM EDT
Uprizing will be playing music that makes you wanna dance! Food truck from That Kitchen $12/person 21+ advance tickets, $15 at the door Under 21 – FREE Gold Leaf Members 2 FREE tickets at the door, no reservations required
Layton’s Chance Vineyard & Winery

Wine & Unwind with Marianna Styles
Sunday, July 30, 2023 from 1:00 PM to 4:00 PM EDT
Sip wine, enjoy live music by Marianna Styles No fee, no reservation.
Layton’s Chance Vineyard & Winery

Summer Concert with Barcode Band
Saturday, August 19, 2023 from 6:00 PM to 9:00 PM EDT
Celebrate this gorgeous summer while dancing on the lawn with Barcode Band! Food truck TBD $12/person 21+ advance tickets, $15 at the door Under 21 – FREE Gold Leaf Members 2 FREE tickets at the door, no reservations required
Layton’s Chance Vineyard & Winery

Sail on the Skipjack Nathan (July 8th)
2023-07-08 10:00 - 12:00

4th of July & fireworks in Cambridge
2023-07-04 20:30 - 22:00
Celebrate Independence Day on the Cambridge waterfront with fireworks over the Choptank River! The best fireworks viewing is at Gerry Boyle Park at Great Marsh, 1 Somerset Ave. in Cambridge, MD. And at Long Wharf Park, High and Water Streets in Cambridge.
Fireworks generally start at dusk, around 9:15pm. Bring your own chairs or blankets and snacks.

Happy 4th of July, everyone!
