There are at least three standard suggestions for shorter walks.
1) Atlantic Highlands (10 miles) - Walk from the start in Matawan to Atlantic Highlands - Henry Hudson Activity Center - Rt 36 - at the end of the basic Henry Hudson Trail before the town of Atlantic Highlands. That's about 10 or 11 miles totally flat on the paved trail which was the old railbed. Best to park a car in the activity center lot and get a ride to the start. (for 20 mile walk) Start by parking there and get a ride back to the car later.
2) Highlands - (13 miles walk) - Park under the bridge on the Highlands. Get ride back to start if you want to end here. (For 17 mile walk) Get ride back from Asbury Park if this is your starting point. Check for carpooling help.
3) Red Bank - (15~ miles) - One mass transit alternative for a good day's walk is to take the train to Red Bank. Try to arrive there around mid-day and then walk either River Road or Rumson Ave eastward to Sea Bright. Its an extra 3-4 miles or the equivalent of walking from the Highlands bridge.
4) Long Branch - (23 miles) - For a 7 mile walk - best to park near the train station and walk a few blocks to the boardwalk area. Follow the schedule so you can meet up with others. Remember, the group will be spread out and you can just walk along the sidewalk or boardwalk toward Asbury Park. Again, follow schedule for approximate times the group will be there.
End Place - The restaurant this year is Asbury Festhalle & Biergarten on Lake St. in Asbury Park where we meet at the end before we catch the train back.