Eastern Shore Vacation Rentals

U.S. Navy Band Cruisers Summer Outdoor Concert Series
2023-07-29 19:00 - 21:00 UTC | MD
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
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

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!

4th of July Parade & Fireworks
2023-07-04 18:30 - 22:00
Join this patriotic salute to our nation with marching bands, fire engines old and new, cars and vans, service clubs, and scouts! ROUTE: The parade kicks off at Amos Garrett and West Street. We’ll head down West Street, the wrong way around Church Circle, and down Main Street. Anywhere along the parade route will provide a good view of the parade.
Annapolis launches its fireworks from a barge in Annapolis Harbor. The best viewing areas include public spaces Northeast of the Severn River, City Dock, along the Naval Academy Bridge (limited parking area), any of the street end parks facing Spa Creek, and aboard a boat in the Annapolis harbor. The Spa Creek Bridge will be closed to traffic from Eastport into Annapolis beginning at 6 p.m. The bridge will remain closed until the conclusion of the fireworks at approximately 10 p.m. Please be aware that the closer you get to downtown, the harder it will be to park and the more difficulty you will have getting out of town after the celebration. Click HERE for a list of parking options from the City of Annapolis.

All You Can Eat July 4th Holiday Crab Cruise on the River Queen
2023-07-04 18:00 - 22:00
Cruise on one of the most exciting attractions offered on Maryland’s Eastern Shore… The Choptank Riverboat Company’s the Choptank River Queen paddle-wheeler.
Ticket includes all you can eat Crabs, Maryland Crab Soup, Fried Chicken, Clam Strips, Corn on the Cob, Cole Slaw, Dessert, Non-Alcoholic Beverages.
Followed by the fireworks around 9:45pm

July 4th Holiday Dinner Cruise
2023-07-04 18:00 - 22:00
Take a relaxing 3-hour cruise and dinner on one of the most exciting attractions offered on Maryland’s Eastern Shore! Followed by a beautiful display of fireworks!!
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 & Crab Cake or Lemon Chicken & Crab Cake. Dinner Side: Potato of the Day, Green Vegetable, Dessert and Non-Alcoholic Beverage
Full Cash Bar on Board as well!

Berlin Fireworks
2023-07-03 20:30 - 21:00
Fireworks start at dusk. Bring lawn chairs, blankets and enjoy. Heron Park is open for viewing.

Event Deta

Fireworks Near You 2023
2023-07-01 20:30 - 2023-07-04 21:00
Add a little extra sparkle and excitement to your vacation with the local area’s fireworks!

Special 4th of July Fireworks Cruise
2023-07-01 20:00 - 22:00
Saturday July 2, 2022 8 PM to 10 PM, $150 per person plus tax and gratuity.
Join us for the ultimate Independence Day celebration and Sail Selina the Ultimate St Michaels 4th of July Fireworks Boat Tour!
Watch in awe as the stunning St. Michaels 4th of July fireworks reflect over the serene Miles River, creating a magical experience you won’t forget. Savor the moment with an open bar featuring the finest icy cold beer, red & white wines, or better yet, champagne. Feel truly pampered on this exclusive excursion.

Book now to secure your spot, as this small-group experience with only 6 guests always sells out fast!
Please call to book us at (410) 726-9400.

Sail on the Skipjack Nathan (July 1st)
2023-07-01 10:00 - 12:00

St. Michaels Ghost Walk - Spirits of Rowdy Women
2023-06-21 20:00 - 2023-11-05 22:00
The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old cemetery and hear stories about St. Mary’s Square where ghosts of unremembered dead once haunted a school that was on the Square. Visit the Victoriana Inn where a spirit of a former guest is still trying to pay his bill. Learn about the ghost in St. Michaels Town Hall, the house of a steamboat captain and a site that was once a brothel is said to still be “active.” The walk is about 1.5 miles and lasts about an hour and a half.

MEETING PLACE: Meet 15 minutes before the start of the tour in front of the Chesapeake Bay Maritime Museum entrance.
TIME & WEATHER: Ghost Walk begins on time. We walk in all kinds of weather except heavy rain and thunder storms. Dress for the weather and be aware that each ghost walk takes at least an hour and covers between 1 and 1.5 miles.

Bring your umbrella if it looks like rain.
Wear comfortable shoes.
Bring a flashlight.
Bring a camera. That’s part of the fun.

Visit (chesapeakeghosts.com) to explore more haunted areas all over the eastern shore!

Father’s Day Riverboat Cruise
2023-06-18 14:00 - 17:00
Take a relaxing 3-hour cruise 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 Prime Rib & Crab Cake or Lemon Chicken & Crab Cake with Vegetable, Potato & Dessert with Full Bar on Board!

Murder Mystery Dinner Cruise (June 17th)
2023-06-17 18:00 - 21:00

Sail on the Skipjack Nathan (June 17th)
2023-06-17 13:00 - 15:00

Annapolis Juneteenth Parade & Festival
2023-06-17 12:00 - 14:00
Come out and join us for our FREE 2nd annual parade and festival on Saturday, June 17, 2023! There will be TWO main stages this year, featuring headliners Avery*Sunshine, Koryn Hawthorne, Pastor Mike Jr., Beverly Crawford, the Chuck Brown Band, and a host of local talent! Fireworks will immediately follow the show!
PARADE- SATURDAY, JUNE 17, 2023​
SUSAN CAMPBELL PARK | CITY DOCK | ANNAPOLIS, MD​
LIBATION CEREMONY: 11:50 AM
PARADE STEPOFF: 12:00 PM SHARP

FESTIVAL-SATURDAY, JUNE 17, 2023
1:00 PM
BATES ATHLETIC COMPLEX
935 SPA ROAD | ANNAPOLIS, MD 21401

Delmarva Pride Presents 2nd Annual Drag Show
2023-06-16 19:00 - 21:00
If you attended last year’s event, you know this show is going to be a wonderful night of entertainment fit for a queen!
As part of its Annual Pride Weekend, the Delmarva Pride Center is presenting its Second Annual Pride Drag Show, hosted by none other than our own Eastern Shore Darling, Miranda Bryant.
Bring your adult friends, your dollars bills, and come see our queens! 100% of ticket sales will go to support the work of the Delmarva Pride Center.
Doors will open at 6:30 p.m. with the show starting at 7 p.m.
Tickets: $30 Tables/Mezzanine; $20 Upper Balcony
All seats for this performance are reserved. The Avalon Theatre is handicap accessible. If you require special seating accommodations, please contact the Avalon Box Office directly 410-822-7299.
Cash bar available.

35th Annual Antique & Classic Boat Festival and Coastal Artisans Fair
2023-06-16 10:00 - 2023-06-18 17:00
One of the largest classic boat shows in the Mid-Atlantic region. On Father’s Day weekend! Featuring the theme, “Your First Love,” members of the Antique & Classic Boat Society-Chesapeake Bay Chapter will show approximately 100 antique and classic cruisers, runabouts and racers in water and on land. Other attractions include educational seminars, maritime vendors, juried artists, nautical flea market, children’s activities, free boat rides, Field of Dreams (boats for sale), great food & more.

Friday, June 16 – 10am-5pm
Saturday, June 17 – 10am-5pm
Sunday, June 18 – 10am-3pm
(All tickets are good for two days. Purchase now for Friday-Saturday or Saturday-Sunday.)

Delmarva Pride Festival
2023-06-16 - 2023-06-18
Delmarva Pride 2023 Delmarva Pride takes place over the weekend 16th to 18th June 2023.

Waterfront Wine & Jazz Dinner
2023-06-14 17:30 - 20:30
Guest( 10 per table) will be greeted with a choice of our sparkling Rosés, Slipstream or Moondance(new), while you settle in, laugh with friends, and feel your entire self begin to relax as you soak in the views accompanied by the melodies of our jazz trio.
Part of the before dinner experience will include wine tasting stations so you can explore all the varietals our beautiful island vineyard helps us create. The coastal soil and fresh bay and river winds leave their special mark on each and every bottle and we want you to have the opportunity to immerse yourself in the full experience.

First course:
Maryland Artisan Goat Cheese, Vermont Sharp Cheddar Fig Jam, Dried Fruits, Seedless Grapes Sliced Baguettes
Salad course:
Mache, Arugula, Mizuna, Red Oak Leaf, Watercress Baby Red Romaine and Frisee Burgundy Amaranth Heirloom Tomatoes and Julienne of Cucumber Blossoms Lemon-Dijon Vinaigrette Dressing
Main Course – your choice of:
Roasted Fillet of Chesapeake Bay Rockfish with Jumbo Lump Maryland Crabmeat Savory Lemon Soufflé Bundle of Haricots Verts Dauphinoise Potato Medallion
Sea Salt and Cracked Black Pepper Roasted Tenderloin of Beef, Medium Rare with Shallot-Wild Mushroom Pinot Noir Sauce Deep Fried Shoestring Sweet Potato Garnish Bundle of Haricots Verts Dauphinoise Potato Medallion
Oven Roasted Vegetables with Extra Virgin Olive Oil & Fresh Garlic Eggplant, Zucchini, Yellow Squash, Portobello Mushrooms, Italian Cipollini Onions Sweet Red and Yellow Peppers Sage Parmesan Polenta and Fresh Basil
And…DESSERT:
Fresh Strawberry Shortcakes English Shortcake Coulis of Fresh Raspberry Whipped Sweet Cream

The Berlin Farmers Market
2023-06-11 08:00 - 2023-09-24 14:00
Only market in the heart of downtown Berlin featuring more than 30 farmers, bakers, food cultivators and more. Shops in the downtown also open early on Sundays.
Live music starts at 10am. Free to attend, free to park!

Farms:

Bennett Orchards: Peaches and Blueberries (in season only)
BayBees Farm: Honey
Assateague Farm: Flowers
Bratten Farm: Locally Grown Produce
Cross Farms: Locally Grown Produce
(Shawn Cross, Market Manager)
Goat Plum Tree Farm: Lettuces, in season fruit and mushroom logs
Splendid Earth Acres Farm: Locally Grown Produce
The Bay Mushrooms Farm: Variety of locally grown mushrooms
6 Kings Farm: Lamb and beeswax products
The Good Farm: Locally grown plants and herbs
Beckys Beanz: Locally grown plants, garden flowers, produce
Marshall Creek Farm: Goat milk items and hand-made wool products
Truitt Farm: Handcrafted hot sauces from their pepper farm

Featuring:

The Buzz Meadery: Variety of locally made mead
Mandala Pies: Pies made from scratch
Little Green Witch Apothecary Teas
Beehouse Soap
Iron Skillet Coffee
Una Bella Salute: Downtown shop offering olive oils and vinegars
baked dessert café: Downtown bakery offering desserts, breads, granola, more
Del’Vecchios Bakery: Variety of baked goods, cookies, breads, more.
Home Canning Classics: Jams, jellies, pickled items, more
Honey Water Candles: Soy candles from local Berlin shop
Lyon Rum: Variety of rum distilled in Easton MD
Bleached Butterfly: Flower arrangements from local Berlin shop
KMBelz Pottery: Locally made pottery
Mother Flowers: Flowers
Sweet Tater Treats for Animals: Locally made for a variety of pets
Clare’s Nutty Concoctions
The Street Kitchen: Food Truck
Krave Gluten Free Bakery
Gather Bakery: Alfajores, Savory Biscuits made from scratch
Pearl Moon Face Painting
Gilberts Provisions: Fresh baked bread, breakfast burritos

Sail on the Skipjack Nathan (June 10th)
2023-06-10 13:00 - 15:00

Tall Ship Kalmar Nyckel Sails in Cambridge (June 4th)
2023-06-04 10:00 - 12:30
Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime!
The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America in 1638.
Day sails on the Kalmar Nyckel offer a unique, hands-on experience where adventure and education come together. You can haul lines, set sails, and hear tales from the crew, or simply relax and enjoy the ship. Kids will enjoy a scavenger hunt and pirate story (costumes welcome).
Tickets are limited and available online (KalmarNyckel.org/explore) or by calling 302.429.7447 for $65 per adult and $40 per child 12 and younger. Advance reservations are highly recommended. The schedule is weather dependent.
