Eastern Shore Vacation Rentals

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.
