This year's John May Mile and 5K run/walk takes place on Saturday, May 9 at Peconic Landing. (Photo Courtesy of Peconic Landing)

FRIDAY 

Paper Rose Workshop | Shelter Island History Museum, 16 South Ferry Road, Shelter Island, 631-749-0025

Learn how to craft paper roses (for Mom or yourself) with artist Catherine Corry from 5:30-7 p.m. in this adults-only class. Tickets are $35 and include all materials. To sign up, click here.

Italian Night Dinner | Townsend Manor Inn, 714 Main Road, Greenport, 631-477-2000

This annual fundraising dinner in support of the Sterling Historical Society happens from 3-8 p.m., with Italian specialties, dessert, coffee and tea, available to eat in or take out. Tickets are $40 per person, $35 for members. For more information and to reserve, check here.

Italian Bred | Suffolk Theater, 118 East Main Street, Riverhead, 631-727-4343

Catch this one-woman show at 8 p.m. by Candice Guardino about her experience growing up Italian in Staten Island, with hilarious impersonations and musical numbers. Tickets are $39-55 and can be had here.

SATURDAY 

John May Mile and 5K Run/Walk | Peconic Landing, 1500 Brecknock Road, Greenport, 631-477-3800

This long-standing race raises funds for the Greenport Fire Department and kicks off at 9 a.m. Cost is $30 for adults, $15 for students with advance registration and $35 for adults and $15 for students on race day. For more info and to sign up, click here.

The 90s Rewind | Greenport American Legion, 102 3rd Street, Greenport, 631-333-2644

Party like it’s 1999 from 7-10 p.m. at this Greenport PTO fundraiser, an adults-only night of music, food and fun with proceeds going to student programs. Tickets are $65 and include a raw bar, appetizer stations, DJ Roc, photobooth and more. To get tickets go here.

Spring Concert | Cutchogue-New Suffolk Free Library, 27550 Main Road, Cutchogue, 631-734-6360

From 2-3 p.m., cellist James Baik and pianist Zhu Wang will perform in the second floor reading room with a reception following the concert. Free, registration required. To register, click here.

SUNDAY 

Lobster Roll + Rosé | Macari Vineyards, 150 Bergen Ave., Mattituck, 631-298-0100

Bring Mom to Macari between 11 a.m.-6 p.m. for a lobster roll and fries from The Catered Fork paired with a glass of rosé or sparkling rosé. Tickets are $70 per person and may be obtained here.

Erin Chase | Terra Vite Winery & Vineyard, 250 Manor Lane, Jamesport, 631-722-3416

Enjoy Long Island singer-songwriter Erin Chase’s tunes from 1:30-4:30 p.m. at this charming vineyard. Free, reservations recommended; to reserve, click here.

Mother’s Day Brunch Clovis Point Vineyard & Winery, 1935 Main Road, Jamesport, 631-722-4222

Clovis Point pairs up with Ammirati’s of Love Lane for this Mother’s Day brunch from noon-3 p.m., with a breakfast station, lunch station, desserts and complimentary glass of wine for moms. Tickets are $40 plus tax, $30 plus tax for wine club members, $20 plus tax for children 14 and under. Seating is limited; to reserve, click here.