St. Michaels Running Festival Half Marathon 10k & 5k

May 17, 2025
St. Michaels
Road
Distances
Half-Marathon, 10k, 5k
Starting Time

7:00 AM

Fees

$75+

Perfect For

Ready to sign up?

500-1000
Fast & Flat
Small Town
High: 84°
/ Low: 68°

Known for its rolling green farm fields, gorgeous homes on the water and a rich, colorful history that dates all the way back before the founding of the nation, this small coastal town in Maryland’s Eastern Shore hosts the 11th annual St. Michaels Running Festival this year, with a half marathon for runners and a 5K for walkers and runners.

The town of St. Michaels played an important role in early colonial America going back all the way to the mid-1600s, when it served first as a trading post for tobacco and fur trappers, and later as an important shipbuilding center, as it lies along the Miles River about halfway between the source of the Susquehenna River to the north and the Atlantic Ocean to the south.

Many of the homes that were built along its seaside streets in that period still stand today, some 200 years later.

In fact, you’re never far from the water when you’re on St. Michaels, it seems, and the half marathon course will take runners near, along and over water at several points during the race, giving runners a chance to take in the scenery that no doubt made it attractive for the filmmakers of both 1998’s Clara’s Heart and 2004’s Wedding Crashers, which featured a number of scenes filmed on the waterfront in and around St. Michaels and nearby Easton, Md.

Runners will start all three races at St. Michaels High School, which lies on Seymour Avenue, less than a mile from the town center.

From there, runners start off by heading first southwest along Seymour and then north along South Talbot Street, which will take them right through the heart of the town and St. Mary’s Square.

This early stretch will also take runners past the town’s famed Cannonball House, which absorbed the impact of a cannonball fired by the British during a battle in the War of 1812, the only house in town to suffer a direct hit — and inspired the town’s nickname as “the town that fooled the British.”

From there, runners continue north and head out of the town center and into more rural terrain, making their way around the fairways of the links golf course near Porter Creek and Hambleton Cove.

They’ll make their way around most of the course, within view of the water all the way around, before heading back to St. Michaels Road, where they’ll then head south back toward town.

Next the race heads west onto Mt. Pleasant Road, which will take runners out on a lollipop-shaped loop through the residential neighborhoods west of St. Michaels, and then heads back into town, where runners will cross the finish line on Fremont Street.

The race is also a fundraiser for the St. Michaels Family YMCA and for the summer programs for kids organized by the St. Michaels Community Center, in addition to a number of other local nonprofits and community organizations.

This race is one of only two Maryland events recognized in the TOP 100 HALF MARATHONS IN THE USA! Our course is built to help you reach a new PR. The first mile takes you through downtown St. Michaels – one of the most picturesque waterfront towns in the region. Once you pass Talbot Street you will run through waterfront communities and down country lanes as you wind your way back towards the downtown area for the finish line celebration. Strollers are not permitted in the half marathon.
Overview
Known for its rolling green farm fields, gorgeous homes on the water and a rich, colorful history that dates all the way back before the founding of the nation, this small coastal town in Maryland’s Eastern Shore hosts the 11th annual St. Michaels Running Festival this year, with a half marathon for runners and a 5K for walkers and runners. The town of St. Michaels played an important role in early colonial America going back all the way to the mid-1600s, when it served first as a trading post for tobacco and fur trappers, and later as an important shipbuilding center, as it lies along the Miles River about halfway between the source of the Susquehenna River to the north and the Atlantic Ocean to the south. Many of the homes that were built along its seaside streets in that period still stand today, some 200 years later. In fact, you’re never far from the water when you’re on St. Michaels, it seems, and the half marathon course will take runners near, along and over water at several points during the race, giving runners a chance to take in the scenery that no doubt made it attractive for the filmmakers of both 1998’s Clara’s Heart and 2004’s Wedding Crashers, which featured a number of scenes filmed on the waterfront in and around St. Michaels and nearby Easton, Md. Runners will start all three races at St. Michaels High School, which lies on Seymour Avenue, less than a mile from the town center. From there, runners start off by heading first southwest along Seymour and then north along South Talbot Street, which will take them right through the heart of the town and St. Mary’s Square. This early stretch will also take runners past the town’s famed Cannonball House, which absorbed the impact of a cannonball fired by the British during a battle in the War of 1812, the only house in town to suffer a direct hit — and inspired the town’s nickname as “the town that fooled the British.” From there, runners continue north and head out of the town center and into more rural terrain, making their way around the fairways of the links golf course near Porter Creek and Hambleton Cove. They’ll make their way around most of the course, within view of the water all the way around, before heading back to St. Michaels Road, where they’ll then head south back toward town. Next the race heads west onto Mt. Pleasant Road, which will take runners out on a lollipop-shaped loop through the residential neighborhoods west of St. Michaels, and then heads back into town, where runners will cross the finish line on Fremont Street. The race is also a fundraiser for the St. Michaels Family YMCA and for the summer programs for kids organized by the St. Michaels Community Center, in addition to a number of other local nonprofits and community organizations.
This race is one of only two Maryland events recognized in the TOP 100 HALF MARATHONS IN THE USA! Our course is built to help you reach a new PR. The first mile takes you through downtown St. Michaels – one of the most picturesque waterfront towns in the region. Once you pass Talbot Street you will run through waterfront communities and down country lanes as you wind your way back towards the downtown area for the finish line celebration. Strollers are not permitted in the half marathon.

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St. Michaels Running Festival Half Marathon 10k & 5k Course Map

Distances
Half Marathon, 10k, 5k
Starting Time

7:00 AM

Fees

$75+

Perfect For

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Train with Runna

Use code HALF for 2 weeks FREE

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