Labor Day signals the unofficial end of summer, and over the long weekend, many will be looking to take advantage of all of the fun stuff to do on Shelter Island.
This extra day off is earned, so let’s make the best of it while supporting some of our local businesses that offer great activities, views, eats, and shopping.
Enjoy these dream day suggestions below, full of ideas to keep the long weekend exciting. And if you’re planning a big end-of-season, party check out our recent post on planning an event.
Dream day: Land and sea
Wake up and pick up the freshly baked croissants you pre-ordered from Marie Eiffel Market. Take a drive around the farm stands at Sylvester Manor, Peeko Oysters, or Southold Bay Oysters.
(On Saturday, don’t miss the Havens Farmers Market at the Shelter Island History Center, 9 AM to 12:30 PM.)
Grab your farm stand ingredients for a picnic lunch to share on the fishing or pleasure charter you booked on Tubby Charters while enjoying Captain John’s tales of the bay.
Finish the night by grabbing a bite to eat and listening to live music at the Shipwreck at Salt Waterfront Bar and Grill, featuring live music Wednesday to Sunday evenings.
Dream day: Views and people-watching
Drop by Stars Café for a freshly baked muffin and specialty coffee, enjoy some of the last days of summer people-watching in the sidewalk cafe tables.
Then hit the links at Shelter Island Country Club for a round of 9 holes on the historic course while taking in some of the best views on the island. For a casual vibe, stay for a cool drink or lunch at The Flying Goat restaurant.
Feeling more of an energetic beach vibe, meander down the hill to Crescent Beach to Sunset Beach Hotel and Restaurant. Ask for a table in the sandpit or top deck for the best beach views and fabulous cars driving by.
If a lobster roll on the beach is more your thing, visit the Roaming Islander food truck, which has a family-friendly menu with ice cream treats, too.
After this, you may feel the day has been full, so end the evening with take-out at home. Enjoy everything from pizza to Vine Street Market specials.
Find dine-in and take-out options listed in the Food and Drink section of our directory.
Dream day: Iconic Shelter Island
No weekend is complete without a breakfast sandwich from the Shelter Island Heights Pharmacy. And every summer should include a paddle on the bay with Kayak Shelter Island.
If you prefer your adventures on land, stop by Piccozzi’s Bike Shop and rent a bike for a 2-wheel cruise around the Island.
Grab some deli platters and drinks from the steadfast Shelter Island IGA for your pre-dinner cinema night in your own backyard.
Yes, folks, Shelter Island Party Rental will supply you with everything you need for your very own “Backyard Movie Night,” including a popcorn machine and candy.
Dream Day: Shopping
Shopping is on the agenda! Buy that gorgeous summer frock you’ve been eyeing in the window all summer. Or, perhaps you want to take advantage of the end-of-season sales or grab some gifts or souvenirs to remember your fabulous weekend.
Explore Marika’s Eclectic Boutique for vintage finds. Check out designer furniture and decor at Fredric Bernstein Design and SIMM’S, with fashion finds, too. Find books, gifts, games, and more, at Finley’s Fiction.
For apparel, jewelry, and accessories, drop by Pure Soul, Mimi Page Jewelry, Kanela Boutique. If you’re in the market for sports apparel, visit Gardiner’s Bay Country Club Pro Shop.
Feeling artisanal and crafty? Check out Sylvester Manor Farmstand and the Havens Gift Shop.
Need a reprieve from shopping? Stop at the new White Oak Wine Garden for a flight of local boutique wines and a cheese plate from the King Andrew Cheese Wagon.
Dream weekend: Guest accommodations
If you’re looking for a place to stay on Shelter Island, we recommend:
- The Dering Harbor Inn – long term stays, pool, tennis, gym, cafe and million-dollar view of Dering Harbor
- Shelter Island House – chic luxury rooms and suites with pool, tranquil garden and on site restaurant with small bites with a latin flair
- West Neck Guest House – boutique charm in renovated farmhouse, private, shares amenities with sister property Shelter Island House
- Sunset Beach Hotel – waterfront beach bungalows, hip scene, boutique and restaurant
