The FIVE-BEACH BIKE TOUR

This tour offers self guided audio

Take in all five of our picturesque beaches, as well as the Southport Harbor on one ride. You’ll be biking past fascinating historical sites, gorgeous water views and some of our popular event spaces as well as the town’s Carl Dickman Par 3 Golf Course. Your ride is mostly on flat terrain and suburban roads for the first seven miles, followed by hilly terrain before it flattens out again in the home stretch.

Starting & Finishing Point: Parking Lot behind Sullivan Independence Hall

Address: 725 Old Post Road, Fairfield, CT 06824 - Sullivan Independence Hall is down the driveway from Fairfield’s Old Town Hall.

Distance: 15.5 miles

Surface: Asphalt

Elevation Gain: Highest - 109ft, Total - 364ft (Five Climbs)

Listen While Touring:

Step-By-Step Directions and Points of Interest:

1) From the Sullivan Independence Hall parking lot, take the driveway on the South side of the Fairfield Museum to Beach Rd

Sullivan independence hall | fairfield museum | beach rd

When the British burned 200+ buildings to punish Fairfield for its rebelliousness in 1779, they spared three homes on the East side of Beach Rd. These homes were said to have billeted British troops. Some think they were spared because the owners were Tories. There could be some truth in both stories.

2) Go right, heading South, on Beach Rd

Old burying ground cemetery - Revolutionary War heroes buried

The “Old Burying Ground” cemetery, where several Revolutionary War heroes are buried, is on your right.

The cemetery is at the South end of the Historic District.

Caleb Brewster (1747 – 1827), a member of George Washington’s Culper spy ring is buried here. Caleb reported to Major Benjamin Tallmadge, an aide to General Washington, and carried messages across Long Island Sound between Tallmadge and the Culper ring's spies on Long Island and in New York City. Caleb Brewster and the Culper spy ring are immortalized in “Turn,” a TV series available through streaming services.

• Gold Selleck Silliman – General in the Colonial army kidnapped by British loyalists in 1779 and held for a year in Long Island before being freed by a prisoner exchange.

• Isaac Jarvis - commanded the fort protecting Black Rock Harbor (now part of Bridgeport) from naval attack. A rough outline of the fort’s foundation can be seen in the water at low tide from St. Mary’s by the Sea at the East end of Black Rock Harbor, which was part of Fairfield at that time.

• Samuel Smedley – Captain of the Defense, a small Patriot frigate which captured a dozen British “prizes.” Sam Smedley eventually was captured by the British, escaped from the infamous Mill Prison in England then returned to Fairfield and fought the British when they raided in July 1779.

3) Continue South on Beach Rd for ½ mile to the intersection with Fairfield Beach Rd

Jennings beach | Sand Castle Play ground | S. Benson Marina

The walkway over the berm at the end of Beach Rd leads to Jennings Beach (beach #1), Fairfield’s largest beach and handicapped accessible from the parking lot. You can walk your bike around the gate on your left, then ride through the parking lot to see more of Jennings Beach, the Sand Castle playground, a fishing jetty and the S. Benson marina, which holds about 600 private power and sail boats. Jennings Beach is free and open to the public, however from Memorial Day Saturday to Labor Day a beach sticker is required to park in the lot.

4) Return to Beach Rd then head West along the shoreline on Fairfield Beach Rd

Fairfield beach club | penfield pavilion

The first building on your left between you and the beach is the 130+ year old Fairfield Beach Club, which is private. Next, you will pass three private homes before coming to Penfield Beach (beach #2) including the Penfield Pavilion, a popular concert and wedding venue.

5) When you reach the intersection with Reef Rd, Fairfield Beach Rd zigs left, then right

Fairfield Beach rd | Pine Creek

(You can cut 1.7 miles off the ride by turning right on Reef Rd). Watch out for speed bumps on Fairfield Beach Rd. About ½ mile down Fairfield Beach Rd, you can see Pine Creek, which looks like a canal, on your right. Continue to the end of the road for an excellent water view and convenient turnaround.

The houses at the West end of Fairfield Beach Rd are about as close to the water as you can get without becoming a houseboat.

6) Return East on Fairfield Beach Rd to Reef Rd. Then head North on Reef Rd toward Downtown Fairfield, left on Oldfield Rd then left on S. Pine Creek Rd

Carl Dickman Golf Course

You will pass the Town of Fairfield’s Carl Dickman golf course on the left side of S. Pine Creek Rd. The Town of Fairfield operates two golf courses. H. Smith Richardson, on Morehouse Highway, is an 18 hole, 6600+ yard par 72/73 course. Carl Dickman is a 9-hole, 1240-yard par 3 course.

7) South Pine Creek Rd dead ends at South Pine Creek Beach (beach #3).

8) Turn around and return North on S. Pine Creek to Oldfield Rd

South Pine Creek | Oldfield Rd

The ride has been flat so far. The hills are next. If you are not up for biking up hills, you can return by going East on Oldfield Rd for 1.3 miles to Sullivan Independent Hall - see step #15 below.

9) Go left on Oldfield Rd, up Sasco Hill

10) Return the way you came up Sasco Hill Rd then take a sharp left on Harbor Rd to cross the Mill River

PEQUOT YACHT CLUB

After crossing the bridge, Harbor Rd bears left and goes up hill.

On the other side of this hill, you will see two large brick buildings on your left overlooking the harbor. These buildings, former onion warehouses, are home to the 100-year-old Pequot Yacht Club. This area was inhabited by the Pequot Tribe centuries ago. European settlers called it Mill River Village which had just a few houses and a wharf in the 1600s. The village, which has a strong connection to the sea, became Southport in the 1800s. Onions and other vegetables, were a major export. Southport was designated a local historic district in 1967.

11) Continue on Harbor Rd with Southport Harbor and Perry Green on your left (another good spot for a water break), to Ye Yacht Yard

Ye Yacht Yard

Ye Yacht Yard is a public marina which can accommodate 65 small boats and 20 kayaks and has a launch ramp and fishing dock. Ye Yacht Yard is another good rest stop.

12) Backtrack 2 blocks on Harbor Rd, go left on Westway Rd then left on Pequot Ave

13) Southport Beach is as far West as you go on this ride. You will be in Westport if you continue West

14) After crossing the Mill River, go right on Sasco Hill Rd. At the top of Sasco Hill, go left on Oldfield Rd

15) Oldfield Rd becomes the Old Post Rd just before you reach the YMCA, the Burr Mansion and the St. Paul’s Episcopal Church on your right

St Pauls episcopal church

St. Paul’s is the site of Fairfield’s first jail. The church was constructed in 1855.

16) Take the driveway after the church to reach the driveway between Fairfield Town Hall and Sullivan Independence Hall