9 a.m. Drive off the ferry and flash back in time. Have breakfast at Stars (17 Grand Ave.), an 1880s-era cottage with great coffee, muffins and scones, as well as breakfast burritos and chorizo-stuffed scrambled eggs.
10 a.m. Walk off the meal with a stroll into “The Heights,” a resort community of Victorian gingerbread cottages, conceived as a Methodist retreat 150 years ago. Climb the sloping, tree-lined streets to Union Chapel (19 Wesley Ave.), a shingled wood-frame structure built in 1875 with marine mosaic windows made of shells, stones, and chunks of glass. The Chequit (23 Grand Ave.) is an another landmark from 1872, once the restaurant for the Methodist camp, now a hotel whose restaurant is overseen by Noah Schwartz of Noah’s in Greenport.
Noon If a warm bowl of salmon chowder or carrot ginger soup with a hunk of crispy baguette on the side are your jam, then head to Marie Eiffel Market (184 North Ferry Road) and enjoy the view from Marie’s harborside picnic tables. For a tuna-melt or the best hash browns ever, visit the lunch counter at Shelter Island Pharmacy (19 Grand Ave.).
1 p.m. Go even deeper into Island history at Sylvester Manor Educational Farm (80 North Ferry Road). The historic plantation dates to 1651, and in wooded areas adjacent to the house, there’s evidence of a Native American settlement that’s even older. Follow the self-guided tour on a system of short trails that loop through the 240 acres of farmland and woodland, past the Manor House and a windmill built in 1810.
3 p.m. There are only 8,000 acres on this seven-mile wide island, and about a third of it is inside the Mashomack Preserve (79 South Ferry Road). The sight of the creeks and bays along Mashomack’s eleven miles of shoreline as seen from the trails is breathtaking as the trees are getting bare. Take the red trail for an easy, scenic two-mile loop.
5 p.m. Staying over? Reserve a room at Ram’s Head Inn (108 Ram Island Drive), a 100-year-old inn perched on a hill above Coecles Harbor. Inside, it’s all country charm from fireplace to French doors, with water views all over. And even if you opt to stay elsewhere, go have a drink on the expansive lawn—the best place on the Island to see the sun set.
7 p.m. Terry Harwood and Lisa Murphy have been making dinner dreams come true at Vine Street Café (41 South Ferry Road) since 2003, and somehow it just gets better every year. Their locally-sourced fish and poultry (crispy duck confit is a house specialty) and the skill and care they express in their food draw people from all forks of life back to their elegant country dining room again and again.