There are lots of off road walks you can take while touring the island. I've numbered them just for reference. They are in no particular order.

#1 - "Seymour's Pond" Reserve - Middle Road to Church Road. 1/2 mile trail organized by the Bermuda Audobon Society. Go past the pond to see some rare old cedar and pepper trees.  Cross over Church Road to the Railway Trail. This will provide great views of Blank Bay and Five Star Island. Southhampton Parish.

#2 - "Warwick Pond" - Middle/Ord  Road or the Railway Trail to Tribe Road #3. Fragrant trees. Nice climb 300 yards up then down to the Pond.  Warwick Parish.

#3 - "Devonshire" - Middle Road (East out of Hamilton). Across from The Old Devonshire Church/Parson Road is the Marsh Firefly Reserve and Freer Cox Memorial. A sanctuary for both flora and fauna run by Audobon and BNT.

#4 - "North Shore" -Front Street West out of Hamilton to Bear left to St. John's/Pitts Bay Road N to Spanish Pt. Road. Check out the view then go back down and continue on Spanish Point Road for a stop at the Admiralty House. If you follow the shady trees you will find Clarence Cove.. Back on the road continue until Black Watch Pass,  there is a gap in the wall with Steep steps that lead to lead to Deep Bay. Devonshire. This is more of a "ride" than a walk and best down on Sunday. You can continue to on North Shore Road to Devonshire Dock where you may be lucky enough to meet some local fisherman and craftspeople. 

#5 - Pembroke Marsh - go through Bernard Park  (Cedar Avenue becomes to Marsh Folly Rd) in Hamilton.

#6 - "East End" After visiting St. David's Lighthouse, head west on Ruth's Bay Road/Orange Hole Road and bear left on Cooper's Island Road to Cooper's Island Nature reserve and Clearwater Beach.