| Saturdays 1:30pm | The Old Field Vineyards' Viticulture and Historical Walking Tour around the 1918 farm with owner Chris Baiz. Some original buildings dating back to the 1850s. | The Old Field Vineyards, Southold | Call 631-765-0004 for more information. |
| Weekends beginning Friday, May 2 through Sunday, May 18 2:00pm-5:00pm | Yan Reiger's Fusion: Contemporary Art Glass exhibition hosted by the Oysterponds Historical Society. This exhibition is free and open to the public. | Oysterponds Historical Society, Orient | Call 631-323-2480 for more information. |
| Saturday, May 17 10:00am | May Mile 2008! The East End's Premier Older Americans Month Celebration at Peconic Landing. Peconic Landing invites you to celebrate the vibrancy, resourcefulness and value of senior adults at this event. Join us for a mile walk on the Peconic Landing campus followed by a BBQ lunch and Carribean band! All proceeds benefit the Greenport Fire Department. The Fire Department will have fire trucks and a working smoke house ongoing through 1:30pm. Entry fee: $10 per adult; $5 children under 12 and adults 65 and older. Rain Date: Sunday, May 18th. | Peconic Landing, Greenport | Call 631-477-3800 ext. 354 to register. |
| Saturday, May 17 10:00am-4:00pm | Arts & Harvest by the Sea at Orient State Park. | Orient State Park, Orient | Call 631-323-2440 for more information. |
| Saturday, May 17 4:00 - 8:00pm | Annual Cocktail Party to benefit the Mattituck FIre Department $50 per person - Dinner, Live Music, Prizes, Beverages and much more!
Tickets available from any Fire Dept. member - or stop by Wendy's Deli on Rte 48, Mattituck
| Mattituck Fire House, Pike and
Wickham Avenues, Mattituck
| Call 631-298-5474 for more information. |
| Saturday, May 17 7:00pm | North Fork Film Festival
Screening of Independent movies, often winners of International Film Festivals wont have the opportunity to see in commercial theatres or say in very limited release large cities only change on the North Fork to see them, movie price = $12 7pm. Wine sold by the glass and gourmet cheese platters will be available for purchase and enjoying during the movie. | Castello Di Borghese, Cutchogue | Call 631-734-5111 for more information. |
| Saturday, May 17 7:30pm | The Arts of Southold Town present: Judy Collins, singer. Concert in Southold High School Auditorium. Tickets are $45 (students-$10). | The Arts of Southold Town, Southold High School Auditorium, Southold | Call 631-734-6320 for more information or to reserve your tickets. |
| Saturday, May 17 1:00pm | Winemakers Walk-
A guided tour of the winery and production facility and wine tasting at Castello di Borghese Vineyard & Winery. $15. pp | Castello Di Borghese, Cutchogue | Call 631-734-5111 to reserve. |
| Sunday, May 18 1:00-3:00pm | Summer is coming Olive Oil Tasting
Taste the flavors of Italy with our very own Oil imported from the family estate in Calabria. Admission is Free.
| Castello Di Borghese, Cutchogue | Call 631-734-5111 for more information. |
| Wednesday, May 21 7:00-9:00pm | Branding, marketing & advertising your nonprofit: Learn how to effectively position your organization, enhance its image and promote its efforts to attract public and foundation dollars. $25 for members, $35 for non-members. Materials fee: $7.50 additional. Please register by May 16th. | Custer Institute and Observatory, Southold | Call 631-765-2626 to reserve. |
| Saturday, May 24 1:00-4:00pm | Reds, Whites and BBQ Blues: music by Kerry Kearney and food by Maple Tree Deli. $10. per person. | Martha Clara Vineyards, Jamesport | Call 631-298-0075 for more information or to reserve. |
| Thursday, May 29 | Golf Benefit for San Simeon by the Sound- Center for Nursing and Rehabilitation | Island's End Golf & Country Club, East Marion | Call 631-477-2110 x251 for more information. |
| Beginning in June | Frisbee/Disc Golf: Enjoy some wine and a little excercise as you test your throwing accuracy with a round of disc golf. | The Old Field Vineyards, Southold | Call 631-765-0004 for more information. |
| Thursday, June 12 5:00-9:00pm | Strawberry Festival hulling night for the community. | Strawberry Fields, Mattituck | Call 631-298-2222 for more information. |
| Friday, June 13 5:00pm-11:00pm | Mattituck Lions Club and Capital One Bank present the 54th Annual Strawberry Festival! Fireworks display at dusk. | Strawberry Fields, Mattituck | Call 631-298-2222 for more information. |
| Saturday, June 14 10:00am-11:00pm | 54th Annual Strawberry Festival! Crowning of the Strawberry Queen will take place at 3:00pm. | Strawberry Fields, Mattituck | Call 631-298-2222 for more information. |
| Sunday, June 15 11:00am-5:00pm | 54th Annual Strawberry Festival! 2nd Annual International Strawberry Shortcake Contest at 1:00pm. | Strawberry Fields, Mattituck | Call 631-298-2222 for more information. |
| Saturday, July 5 9:00am-4:30pm | Cutchogue-New Suffolk Historical Council's 44th Annual Antique Show and Sale! Seventy-eight dealers, rain or shine, at the Village Green on the Main Road in Cutchogue. All exhibits for sale, snack bar, home-made bake table. Admission $5.00. Early Birds 7:30am-9:00am (admission $10.00). | Village Green, Cutchogue | Call 631-734-2608 for more information. |
| Saturday, July 12 10:00am-4:00pm | Mattituck Chamber of Commerce Street Fair on Love Lane in Mattituck! Vendors, food, Little Miss Mattituck Competition and live entertainment. | Love Lane, Mattituck | Contact mattituckchamber.org or call 631-298-9400 for more information.
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| Saturday, July 19 7:30pm | The Arts of Southold Town present: Paquito d'Rivera, Jazz concert at the Southold High School Auditorium. Tickets $45 (students-$10). | The Arts of Southold Town, Southold High School Auditorium, Southold | Call 631-734-6320 for more information or to reserve your tickets. |
| August (Saturday date to be announced) 7:30pm | The Arts of Southold Town present: The Perlman Music Program at the Southold High School Auditorium. Tickets $20 (students-free) | The Arts of Southold Town, Southold High School Auditorium, Southold | Call 631-734-6320 for more information or to reserve your tickets. |
| Saturday, October 4 and Sunday, October 5 10:00am-5:00pm | The Hallockville Museum Farm 28th Annual Fall Festival! The Festival will feature over 50 craftspeople displaying their unique handmade folk art, demonstrations of wool spinning, weaving, quilting, knitting, rug hooking, chair caning, basket making, decoy and woodcarving. Other crowd-pleasing activities include an antique tractor pull, hayrides, food, music, childrens activities, livestock displays, an old-fashioned storyteller and tours of our historic farmstead. Taste and enjoy some of the East Ends premier wines.Admission is $7 for adults, $5 for children (5 12 years) and seniors. A special family (mom, dad and their children) pass is available for $18.
| Hallockville Museum Farm, Jamesport | More information is available at www.hallockville.com or 631-298-5292. |
| Saturday, November 1 7:30pm | The Arts of Southold Town present: Claire Bloom, Actress at the Southold High School Auditorium. Tickets $30 (students-free) | The Arts of Southold Town, Southold High School Auditorium, Southold | Call 631-734-6320 for more information or to reserve your tickets. |