2025 Summer Guide to Maryland’s Eastern Shore

Welcome summer in style with unforgettable experiences across Maryland’s Eastern Shore. Whether you're seeking coastal festivals, historic charm, family fun, or fresh-caught crabs by the water, there's something for everyone in this vibrant region.

🍷 Maryland Crafted: Centreville

📍 Centreville, MD  |  June 7, 2025

Celebrate local creativity at this artisan showcase, formerly known as DrinkMaryland. Enjoy craft beverages, food trucks, over 40 Maryland vendors, and live music in Centreville’s charming town center.

🏊 IRONMAN 70.3 Eagleman Triathlon

📍 Cambridge, MD  |  June 8, 2025

This world-renowned triathlon weaves through the scenic Chesapeake Bay and Blackwater National Wildlife Refuge. Witness elite athletes tackle a 1.2-mile swim, 56-mile bike, and 13.1-mile run.

⛵️ Antique & Classic Boat Festival

📍 Chesapeake Bay Maritime Museum, St. Michaels  |  June 13–15, 2025

Step back in time with vintage vessels and fishing boats docked in the scenic harbor of St. Michaels. This annual event includes coastal vendors, maritime art, and family activities.

💜 Smokey Cat Lavender Festival

📍 Federalsburg, MD  |  June 14, 2025 | ⏰ 10 AM – 4 PM

Enjoy the scent of summer at this family-friendly festival. Highlights include U-pick lavender, craft vendors, live music, food, and a petting zoo—all in a charming country setting.

🎆 Fourth of July Fireworks

Celebrate Independence Day across the Shore! Local firework displays and festivities light up the sky in:

• 🎇 Cambridge - Gerry Boyle Park

• 🎇 Salisbury - James M. Bennet High School

• 🎇 Easton - Easton Pkwy/ St. Michaels Rd

• 🎇 Rock Hall - Rock Hall Harbor

• 🎇 Kent Island - Kent Narrows

• 🎇 Ocean City - N. Division St & 125th St

• 🎇 Oxford - Tred Avon River

• 🎇 St. Michaels - St. Michaels Harbor

• 🎇 Chestertown - Wilmer Park Waterfront

Bring a blanket, find your favorite waterfront view, and enjoy the show.

🎨 Plein Air Easton

📍 Easton, MD  |  July 11–20, 2025

As the largest plein air painting competition in the U.S., Plein Air Easton invites artists from around the globe to create stunning works on-site. Wander downtown Easton and watch masterpieces unfold in real time.

🍑 Sudlersville Peach Festival

📍 Godfrey’s Farm, Sudlersville  |  August 1–2, 2025

Savor the sweetness of summer with live music, homemade treats, crafts, and fun for all ages in Queen Anne’s County.

🏴‍☠️ Pirates & Wenches Weekend

📍 Rock Hall Harbor  |  August 8–10, 2025

Set sail for adventure in Rock Hall with pirate-themed games, costumes, live entertainment, and waterfront revelry.

🎉 Caroline Summerfest

📍 Downtown Denton  |  August 15–16, 2025

A family favorite! This free festival features a marching band battle, fireworks, food trucks, artisans, and activities for kids.

🍽️ Waterfront Dining Destinations

Savor fresh seafood and spectacular views at these top waterfront restaurants:

• Portside Seafood Restaurant – Cambridge

• Foxy’s Harbor Grille – St. Michaels

• Suicide Bridge Restaurant – Hurlock

• Libbey’s Coastal Kitchen – Stevensville

• The Jetty – Grasonville

• The Crab Claw – St. Michaels

• Doc's Sunset Grille – Oxford

• Waterman’s Crab House – Rock Hall

Free Outdoor Summer Activities

🎥 Outdoor Movies in Easton

Family-friendly films under the stars all summer. Movie starts at 8:30 PM or dusk. Visit discovereaston.com for the full schedule.

🎶 Concerts in the Park – St. Michaels

Enjoy Thursday evening live music at Muskrat Park, starting at 6 PM.

🌆 Local Nights Out

• Third Thursdays – Denton: Live music, local dining, corn hole, and shopping.

• First Fridays – Easton: Art gallery openings and happy hour specials.

• Second Saturdays – Cambridge: Evening art receptions and shopping downtown.

🛶 Get on the Water

Rent a kayak or paddleboard and explore the rivers and creeks:

• Shore Pedal & Paddle – St. Michaels

• Blackwater Adventures – Cambridge

• Chester River Kayak Adventures – Rock Hall

• Tilghman Island Rentals – Tilghman Island

⚓ Marinas

Charming marinas for docking and waterside enjoyment.

• Cambridge Yacht Basin - 2 Yacht Club Dr, Cambridge, MD

• Easton Point Marina - 975 Port St, Easton, MD

• Safe Harbor Great Oak Landing - 22170 Great Oak Landing Rd, Chestertown, MD

• St. Michaels Marina LLC – 305 Mulberry St, St. Michaels, MD

• Safe Harbor Narrows Point -  428 Kent Narrow Way N, Grasonville, MD 

🌳 Parks to Explore

• Sailwinds Park – Cambridge

• Idlewild Park – Easton

• Wilmer Park – Chestertown

• Chambers Park – Federalsburg

• Millstream Park – Centreville

• Muskrat Park – St. Michaels

🍦 Ice Cream Stops Worth the Detour

• The Scottish Highland Creamery 

• Bonheur Ice Cream & Pie

• Stam’s Luncheonette 

• Storm & Daughters Ice Cream 

• Commerce Street Creamery Cafe

• Bullock’s Deli

🦀 Where to Find Local Crabs by County

Dorchester

• JM Clayton Co.

• KOOL Ice

• Choptank River Crab & Oyster Co.

• Lindy’s Seafood

• Danny’s Soft Crabs

Caroline

• LNT Seafood

• Blough’s Seafood

Talbot

• Gay’s Seafood

• T.L. Morris

• Chesapeake Landing

• Crab Shack

• Cole’s Seafood House

Queen Anne’s

• Stevensville Crab Shack

• Harris Crab House

• Cranky Crab

• Hunter’s Seafood Market

Kent

• Clark’s Seafood

• Ford’s Seafood

• Chester River Seafood