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Hop the ferry to The Rock. (Credit: Matt Rohde)

Looking for something to do on Shelter Island this spring?

A quick ferry ride will transport you to delicious dinners, live music and peace of mind. Fill your calendar with these events as you discover all The Rock has to offer this season.

A New Chef at Isola

One of Shelter Island’s coziest restaurants (and one of the few open year round) has a new executive chef. Originally from Ecuador, Chef Sixto Coronel trained in Italian cooking under renowned Chef Frank DeCarlo of the former Barba Bianca in Greenport, as well as Chef Mario Bitali and Chef Michael White. Chef Sixto worked with Isola last summer and is now back creating new dishes, including his homemade squid ink tagliolini and shrimp in a cherry tomato sauce, and homemade gnocchi with mushrooms in brown butter and sage.

Isola is known for its wood-fired brick oven, where many of its dishes are finished. In addition to Italian classics, owner Brad Kitkowski said the restaurant will be rolling out new dishes every week with a “strong focus on local seafood, locally sourced produce and fresh pasta this season.” Isola is also hosting live music on select Saturday nights during dinnertime. Previous performers include Julia King and Sara Mundy.

15 Grand Ave, Shelter Island, 631-749-9036

Live Music at the Ram’s Head Inn

The Ram’s Head Inn, under new ownership this spring, is offering live music on select weekend evenings during the spring. Live music is in the lounge beginning at 6:30pm. Most recent musicians who have performed include Lizzie and the Makers, Who Are Those Guys, and Greg McMullen & Julia King.

Dinner service is currently Thursday-Sunday from 5-9pm. Lunch is served on Saturdays from 11:30am-2pm, light fare from 2-5pm at the bar. On Sundays, brunch and lunch are served from 11am-2:30pm, and light fare is served from 2:30-5pm.

108 S Ram Island Dr, Shelter Island, 631-749-0811

Dinner at Vine Street Café

Tis’ the season for graduations, Mother’s Day and Father’s Day — show them that you care with dinner at Vine Street Café. In addition to a special spring brunch menu, the restaurant is open for dinner service starting at 5:00 pm. Weekly, rotating specials include escargot Nero with local escargot and cote de beouf. Back by popular demand is their all-night 3-course prix fixe menu. (That menu is also available to go.)

Takeout may be picked up at The VSC Market along with their Little Wine Shop Popup, offering a curated selection of wine from all over the globe. The market is currently open Thursday-Monday from 2-8pm.

41 South Ferry Rd, Shelter Island, 631-749-3210

Hiking at Mashomack Preserve

As the warmer weather arrives on our doorstep, disconnect from your schedule and explore the vast natural surroundings of this preserve along 11 miles of coastline. During your walk, see how many different types of plants, trees, and wildlife animals you spot. As spring is now upon us, you may spot some baby red fox and deer, as well as box turtles, possum, and many more iconic species. Visit to download a trail map. The preserve is open Wednesday-Monday from 8am-6pm. Closed on Tuesdays.

79 S Ferry Rd, Shelter Island, 631-749-1001

Barre classes at Shelter Island Pilates & Barre

Stretch out this spring with their class pack special: buy a 5-pack of live classes, and receive a free on demand class. Live classes are currently scheduled on Tuesdays, Thursdays, and Saturdays. Current COVID-19 safety compliances include regular professional cleaning cycles, reducing the number of clients inside, and maintaining separate entrances and exits from the building.  Virtual and private classes are also available.

57 N Ferry Rd, Shelter Island, 917-620-4155

A virtual Cinco de Mayo festival 

The Shelter Island Public Library will host a virtual food festival with Simply Creative Chef Rob Scott to help celebrate Cinco De Mayo on Monday, May 3 from 7-8pm. Ingredients will be posted on the library’s Facebook page. The video from the festival will be up for the month of May to reference and for cooking along.

Additional virtual adult programs include a string quartet performance by Twin Forks Musicivic on Friday May 14 at 7pm; Vegetable Gardening 101 workshop with Cristina Cosentino of Sylvester Manor on Saturday, May 1 at 4pm; and What’s It Worth antique appraising on Saturday, May 8 from  10:45 am-1 pm.

The library will be hosting some in-person events this summer outside under a tent. When visiting the library in person, there is a time limit of 45 minutes due to current COVID regulations.

37 N Ferry Rd, Shelter Island, 631-749-0042