The East Side of Stamford is the best area to run in Stamford. This route strings together a couple of nice parks and waterfront paths. It’s up to 6 miles one-way, so do it all or choose a section! 

From WWE Headquarters just off Rt. 1, run along Holly Pond on Weed Ave. for 1 mile (note: narrow shoulder) to Cove Island. A loop around the Island is ~1 mile. Then it’s about 1 mile west to Cummings Park, which at 79 acres has a boardwalk and fishing pier. Turn around here for a ~6-7 mile run. Or add-on the 2 miles down to Shippan Point along Ocean View Ave.  This area has lovely homes and good water views at the point. 

Add-Ons:  Enjoy some of the neighborhood streets of Shippan Point, with its waterfront properties and historic homes. It’s a nice run to combine the neighborhood with Cummings Park and the short, scenic path along Halloween Basin down to the beach.