The countryside around Ipswich is still preserved from development, and you are unlikely to see much traffic on these roads. The area you’ll ride across could be called horse country, and chances are you’ll see more than a horseback rider training on the many farms that dot the area. The extension to Great Island will bring you to an often-overlooked beach over the Ipswich River, directly across Crane Beach. In just one ride, this is a chance to go from deep green to deep blue, and without wasting too much of your energy since the ride is almost flat.
At average speed, the complete loop should take about 4 hours including stops.

Here are the detailed ride directions:
From Wenham Church, take left on Route 1A for one third of a mile
Turn right on Larch road, which becomes Essex Road
At an intersection with sign for Route 22, turn left on Woodbury Road (no street sign)
Turn right on Bridge Street after short descent
Turn left on Sagamore Street (visible, old-fashioned street sign)
At the end of Sagamore Street (golf course on left), turn right on Route 133
Half a mile down Route 133, turn left on Northgate Road (this is a dangerous intersection; stop on the road shoulder to check traffic before turning)
At next intersection, turn left on Argilia Road. Less than a mile later is the small Hamlin Reservation on the right. This is a nice place for a rest stop or a short walk in the nearby Great Marsh
At the stop sign, turn right and go straight on Jeffreys Moore road. If you do not want to visit Great Island, which adds 9 miles to the ride, go right at the stop sign, stay on the main road turning left, and take left at the next large intersection on Topsfield road
If you go to Great Island, continue straight until you reach the island, actually a narrow peninsula in the marshes ending in a large hill; stay on the right until you reach the beach (obvious parking lot in front of you); the road ends a few yards on the right at a private housing community. The beach slopes down to the Essex River opening out to the ocean, with great views of Crane Beach on the other side of the bay.
From the beach, take right on Bayview road and always stay close to the water; at a fork, take right down and cross a short valley under a large rectangular building on top of a hill.
You will soon reach Jeffreys Moore road again; ride back the way you came towards Ipswich; before reaching the town center, turn right on East Street after a short climb (large tree and small wooden garage shack at the intersection), then immediately left on North Main Road
At the main intersection down in Ipswich, go straight on Topsfield Road
Turn left on Mill Street (large traffic sign); From this point, the ride is mostly in the woods and very shady. You will also ride past Appleton Grass Rides (on the left side, sign and parking lot), a very nice reservation that is a great place for a walk.
Stay on Mill Street until you reach your departure point at the Wenham church.