Start at the historical Plymouth Rock and take a stroll through beautiful downtown Plymouth. Walk along the water, enjoy the weather, stop into all the little shops along the strip, grab an icecream at Ziggy's or Peaceful Meadows or grab a drink and some dinner at one of the many delicious restaurants all with outdoor seating and beautiful views. Some of my favorite restaurants down in Plymouth are East Bay Grille, Waterfront Bar & Grille, Cabby Shack and Tavern on the Wharf.
Start at Plymouth Rock but head to the opposite direction than the restaurants and take a beautiful walk through Brewster Gardens. Take the path all the way down and you will bump into Luciano's Pub-Sports Bar.
Located behind East Bay Grille. The jetty is another fun walk with beautiful views. It may be chilly in October but bundle up and head there, it will be worth it!
Head to Plymouth Bay Winery and enjoy a wine tasting with a side of cheese and crackers! This is also located in downtown Plymouth so add this to your list of places to stop!
Looking to do a little retail therapy? Head to Colony Place where there are countless places to shop and several places to eat!
Located at the Kingston Mall. Pinz is a fun spot to eat, drink, bowl, ax throw, play shuffle board and arcade games!