St. Michaels, MD, Activities 

Things to Do in St. Michaels, MD 

The beauty of our Chesapeake Bay location on the Eastern Shore of Maryland is that there’s plenty to do, even for those who wish to not do a thing. Relax by the bayside at Wades Point Inn and enjoy the sunrise with a cup of coffee. Or, stay right here and take advantage of our complimentary bikes and kayaks. Or, cast a line off of our shoreline. Feeling even more adventurous? Take a refreshing dip off the dock. 

Our St. Michaels, MD, bed and breakfast boast the quintessential serenity and peace of the Eastern Shore right on our property. However, don’t miss out on the wonderful St. Michaels, MD, activities in town. Experience St. Michaels as the locals do with our finest recommendations below. For more suggestions and free help planning your vacation, request a copy of our complimentary Vacation Guide

Your Guide to St. Michaels Activities


Best St. Michaels, MD, Activities at Wades Point Inn 

Biking

Our St. Michaels, MD, bed and breakfast’s property is mostly flat. This level ground allows you to see for miles. Take in views of the Chesapeake Bay kissing the sky as you pedal along on one of our complimentary bikes. Inquire at the front desk.

Bird & Wildlife Watching

What species will you spot during your time at Wades Point Inn? Check the “Birds of Wades Point Inn” bulletin on the refrigerator in the guest kitchen for an up-to-date list of resident species. Our friends at the Tabolt Bird Club are always adding new species!

Kayaking

Those kayaks out by cove aren’t just for show! Registered guests are welcome to take advantage of these single and tandem kayaks to explore our corner of the Chesapeake Bay. Inquire at the front desk.

Fishing

Feel free to toss a line in the water right off of our shoreline for an afternoon or relaxation by the bay. Or, for more challenge, try your luck at the best fishing waters for rockfish and bluefish. Right off of Wades Point Inn, a certified Orvis guide will take you out in a 19-foot Hewes flatboat.

Swimming

The ladder off of the swim dock leads you into the shallow water of the bay with a mostly sandy bottom. Swimming is delightful till the jellyfish come in. However, float above them on inflatable rafts and lounge chairs for an equally as cooling and enjoyable afternoon on the water. 

Also available is Bay Hundred Pool on North Talbot Street in St Michaels. 

Contact: 410-745-6592.


Best St. Michaels, MD, Activities in the Area 

Boating

Embark on a Voyage of Discovery: Aboard the M/V SHARPS ISLAND, you will be taken back through the storied history of the Chesapeake Bay and its lighthouses. Four different Chesapeake Lights trips accommodate any schedule and all levels of interest. Each includes a narrated recounting of The Bay’s history as well as informed local insights about its fragile and beautiful ecosystem. 

Contact: 410-886-2215

Lady Patty sets sail from Knapp’s Narrows Marina onto the Chesapeake Bay and the Choptank River.  They have beautiful sunset sails and spectacular day sails. They will offer discounts for those staying at Wades Point.

If you prefer to sail on a historic Skipjack, then Captain Ed Farley and H.M Krentz await your call. Docked in St Michaels. 

Contact: 410-745-6080

Skipjack H. M. Krentz: Sailing on the H. M. Krentz. Daily 2 hour sailing schedule 11:00 AM, 2 PM, evening to sunset. Departs from the Chesapeake Bay Maritime Museum in St. Michaels. Admission charge. 

Contact: 410-745-6080

A National Historic Landmark: Skipjack Rebecca T. Ruark

Sail aboard the oldest working skipjack on the Chesapeake Bay, built in 1886. Enjoy nautical tales and ecology stories from 5th-generation and world-renowned Capt. Wade H. Murphy, Jr.

Sail Aboard the Selena II: Daily sailing schedule 10 AM; 12:30 PM; & 3 PM. Admission charge. Sunset Champagne Cruise 5:30-7:30 PM. Moonlight Sail 8-10 PM. Wine Tasting Cruise. Private Sailing Lessons, private charters, & catering available. Departs St. Michaels Harbour, St. Michaels. Admission charges do not include the 10% St. Michaels amusement tax nor gratuities. Contact: 410-726-9400.

Charter Boat Fishing

Captain Bobby Marshall: This captain sets sail from Tilghman Island.  

Contact: 410-924-4201 

Cruises

The Patriot:  Take a leisurely cruise up the Miles River aboard the climate-controlled Patriot while you listen to a historic narration of Talbot County. 

Contact: 410-745-3100.

Poplar Island Tours: A fascinating look at a rebuilt island that is an important link in the ecological chain that anchors the Chesapeake’s incomparably rich natural bounty.

Contact Katelin Mielke, Poplar Island Tour Director 

Email: katelinmielke@earthlink.net

Phone: 410-770-6503

 *Tours run on a reservation basis only.

Kayaking

Tilghman Island Water Trail: From the Maryland Department of Natural Resources: The American Canoe Association (ACA) has named the Tilghman Island Water Trail in Talbot County as an “ACA-Recommended Water Trail” for 2006. The Trail joins 11 other trails across the United States in receiving this national distinction. 

Contact: Eastern Shore Adventures, Easton, MD (410) 820-8881

Wildlife & Birdwatching

Pickering Creek Audubon Center: A private, non-profit sanctuary of the Chesapeake Audubon Society. You will find 400 acres of protected, hardwood forest, non-tidal wetland, wildlife, plants and nature preserve. Field trips, canoe rentals, and displays are available. 

Contact: 410-822-4903.

Blackwater National Wildlife Refuge: Located just a short distance to the south in Dorchester County and has 23,0000 acres of tidal marsh for migratory birds. 

Contact: 410-228-2677

*If you are interested in birding you can join with the local chapter of the Maryland Ornithological Society for one of their nature walks. 

Contact Les Roslund at 410-763-8169.

Bicycling

Tabolt County: Our area features more than 180 miles of themed bike trails. In fact, Wades Point Inn is part of the “Chesapeake Views” path!

Golf

Harbourtowne Golf Resort: Located 5 miles from our St. Micheals, Md, bed and breakfast and is an 18-hole, par 70, Pete Dye-designed championship course. 

Contact: 410-7745-9066

Hog Neck Gold Course: Located in Easton, this course is rated among the “Top 25 Public Golf Courses in the Country” by Golf Digest and is a par 72, 18-hole course as well as a par 32 Executive Nine Hole Course. 

Contact: 410-822-6079.

The Easton Club: Located in Easton, is a par 72, 18-hole championship course for public play featuring 6,700 yards of unique challenges for all levels of golfers. 

Contact: 410-820-9100

Entertainment: Arts, Theatre & Museums

The Chesapeake Bay Maritime Museum

Contact: 410-745-2916

The Academy of Art Museum

Contact: 410-822-2787

St. Mary’s Square Museum

Contact: 410-745-9561

Historic Avalon Theatre 

Contact: 410-822-0773

Tred Avon Players Inc. (TAP)

A non-profit Maryland corporation, organized in 1982 to present plays and musicals in the then newly-renovated Oxford Community Center (OCC).


St. Michaels, MD, Events 

Best St. Michaels, MD, Events by Season

Each season in St. Michaels features something uniquely different. From holiday-themed events to monthly recurring arts events, there’s something to do for locals and visitors alike. Check out the index of recurring items below, then check out one exciting event each month! For more monthly happenings and annual events, request a copy of our complimentary Vacation Guide

Your Guide to St. Michaels Events

First Friday Gallery Walk (Recurring monthly): Enjoy the exhibits at galleries, shops, and restaurants in Easton’s Town Center the first Friday evening of each month. Refreshments and discussion are available at several galleries and many stores stay open late, (5 p.m. to 9 p.m.), so plan to make an evening of it! 

Contact: 410-770-8350.

Historical Society of Talbot County Historic Homes Tour (April. through Nov.): The only homes regularly open to the public are the three on the property of the Historical Society of Talbot County. The homes of Joseph Neall, c 1795, and James Neall, c 1805, and the studio of Chandlee Forman, a replica colonial home, are open to the public every Friday, April through November, at 11:30 AM. Address: 25 S. Washington Street, Easton. Admission charge $5. 

Contact: 410-822-0773

Concerts in the Park (June through Aug.): Live music in Muskrat Park Thursday evenings from 6:30 p.m. to 8:00 p.m. 

Contact: 410-745-6073

St. Michaels Farmers’ Market (May through Oct.): Stop in for fresh produce and other locally-made items from 8:00 a.m. to 12:00 p.m. on Saturday mornings. Located on Green Street at Muskrat Park. 

Winter

December

Christmas in St. Michaels: Annual celebration of the season featuring ticketed events that benefit the local community. 

Spring

March

Daffodil Festival: Weekend-long celebration welcoming the newly-planted spring flowers with parades, contests, awards, and more. 

April 

Eastern Shore Sea Glass & Coastal Arts Festival: Two-day festival with fun attractions like live music, history seminars, and more. Check out for-sale products by local artisans. 

May

Multicultural Festival: Annual event that embraces all of the different walks of life in St. Michaels. 

Summer 

June 

St. Michaels Brewfest: Have your taste of more than 100 locally-fermented brews, listen to live music, and just have a good time to start your summer!

July

Tilghman Island Seafood Festival: Taste the freshest catches and place your best on a crab race!

August

Watermen’s Appreciation Day: Annual fundraising event that features a boat docking contest, fresh steamed Maryland blue crab, food vendors, games, and more. 

Fall 

September 

Ride for Clean Rivers: Cycling event that benefits ShoreRivers and their mission to “Restore Eastern Shore waterways through science-based advocacy, restoration, and education.”

October 

Oysterfest: Exactly what it sounds like. Come shuck with us!

November

Waterfowl Festival: A celebration of our maritime heritage. Enjoy dock dogs, food and drink vendors, duck-calling contests, and more!