Eastern Shore Vacation Rentals

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.

Paint The Town Show + Sale
2026-04-25 17:30 - 20:30 (America/New_York) | 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.
