Year Round Activities on the East End

Montauk Point Lighthouse

The North and South Forks of Long Island offer a vibrant array of events throughout the year, attracting both residents and visitors alike. From fairs to festivals, these gatherings showcase the region’s rich culture and history while providing entertainment for all ages. We have curated a list highlighting some of the regional activities by month. 

*This list has been updated to accommodate the 2024 calendar


HarborFrost  |  Sag Harbor  
2/3 | 2:30p – 9p
HarborFrost embodies the essence of winter in Sag Harbor! Experience captivating live ice carving demonstrations, enchanting ice sculptures lining Main Street, lively musical performances, and engaging indoor activities for children. The celebration reaches its pinnacle with the breathtaking Fireworks by Grucci spectacle illuminating the skies off the end of Long Wharf. 

WinterFest  |  Southold 
WinterFest welcomes both residents and visitors, completely free of charge. The event showcases local businesses and organizations, along with entertainment, complimentary food and beverages, and a variety of activities tailored for adults and children. Special attractions include DJ music, caricature artists, face painting, captivating ice sculpting, jugglers, live music, and many other surprises!


Montauk Music Festival  
5/16 – 5/19
The Montauk Music Festival is organized by the Montauk Chamber of Commerce and typically takes place the weekend preceding Memorial Day. This vibrant celebration of music offers an extensive lineup of activities and events suitable for all ages.

Featuring approximately 400 live music performances across 40 venues over four days, including two days at the iconic Lighthouse, the festival provides a diverse musical experience. spanning various genres such as rock, folk, blues, and jazz. Attendees can also indulge in local culinary delights and refreshing beverages offered by numerous food and drink vendors.

Mosaic Festival  |  Riverhead
5/26 | 12p – 5p
During a single day, East End Arts transforms Riverhead’s Main Street area alongside the Peconic River into a vibrant celebration of creativity. The Mosaic Festival attracts artists, musicians, and art enthusiasts of all ages to either participate or observe as artists turning squares of the street into captivating and dynamic works of art.

It’s an occasion for leisurely strolls, enjoying the fresh air, witnessing artists in their element, and engaging in family-friendly activities.


Mattituck Lions Strawberry Festival 
6/12 – 6/16
Wed &Thurs  5p – 10p | Fri 5p – 11p | Sat 11a – 11p | Sun 11a – 5p
The Mattituck Lions Strawberry Festival, organized by the Mattituck Lions Club, typically occurs in early summer, often during June’s Father’s Day weekend. This celebration of the strawberry harvest offers a variety of activities for all ages, including sampling strawberry-themed treats from food and drink vendors, enjoying live music, browsing arts and crafts stalls, and exploring the farmers market. Highlighted by the “Strawberry Festival Talent Show” and family-friendly carnival rides, the festival provides a fun day out while supporting the local community. It’s a must-visit for food enthusiasts and those seeking wholesome entertainment. Please note, this alcohol-free event doesn’t allow pets unless they are service animals.

Reflextions Riverhead  |  Grangebel Park, Downtown Riverhead
6/29  |  8/3  |  9/7
6p – 10p
Held multiple times throughout the summer, Reflextions Riverhead, Art in The Park, is a walkable, interactive experience for visitors. With a scenic setting utilizing and showcasing the riverfront park, Reflextions creates a free, accessible public art space. Reflextions consists of a daytime component as a standalone reflective art display, but at the special nighttime events, the magic comes to life when the art pieces are illuminated.  Featuring assorted elements of“LIGHT”, based on artist interpretations and designs. Elements of light include LED, Incandescent, Fire, Black light, Day Glow and photo luminescent displays. Each Illumination event will showcase additional lighted exhibits and live performing arts. Visit their website for the music lineup at each event. 


Alive on 25  |  Main Street, Riverhead 
7/5 (rain date 7/9) and  8/9 (rain date 8/23) | 5p – 9:30p
Alive on 25 is a vibrant summer street festival, free for all to enjoy, boasting live music across multiple stages. This lively event showcases a diverse array of attractions, including a car show, bustling street vendors, enticing food trucks,craft beverages, engaging kids’ activities, and captivating street performers. Traditionally, it commences with spectacular fireworks over Grangebel Park during the 4th of July holiday, setting the stage for a memorable celebration.

Summer Concert Series
From the end of June to August, the East End resonates with the sounds of music. Each week, a handful of our towns host free outdoor music events for all to enjoy. Explore the East End Getaway calendar for artist lineups and performance specifics.
Monday nights
Mitchell Park, Greenport  |  7:30p
Village Green, Montauk  |  6p
Tuesday nights
Village Green, East Quogue  |  7p
Wednesday nights
Agawam Park, Southampton  |  6:30p
Thursday nights
Good Ground Park, Hampton Bays  |  7p
Village Green, Westhampton Beach  |  7:30p


Cardboard Boat Races  |  Peconic Riverfront, Riverhead  
8/3 (rain date 8/10) | 9a – 2p
The Cardboard Boat Races are an annual tradition hosted by the Riverhead Chamber of Commerce that usually occurs on a mid-August Saturday, with a rain date set for the following Saturday. This delightful outdoor event welcomes both visitors and locals of the East End to construct their own cardboard boats using duct tape and put their creations to the test by racing them down the Peconic River. Prizes await winners in different categories, adding to the excitement. Additionally, the day is filled with a diverse range of games and activities for all to enjoy.

Polish Town Fair   |  Polish Town, Riverhead  
8/17 – 8/18 | 10a – 6p
Polish Town Fair  gives locals and visitors alike the chance to indulge in authentic Polish cuisine, groove to live music and explore handcrafted Polish artisan vendors.

Hamptons Classic  
8/25 – 9/1
The Hampton Classic Horse Show, an esteemed annual event on Long Island’s East End, stands as one of the premier equestrian gatherings in the United States, typically spanning a week in late August or early September. Drawing elite riders and horses worldwide, it offers a diverse array of classes and competitions for attendees of all ages. Featuring hunter, jumper, and equitation classes alongside prestigious Grand Prix events, the show also presents family-friendly activities like pony rides, face painting, and a petting zoo. A highlight is the gripping “Grand Prix”, where top riders vie for supremacy. Special attractions include the upscale “VIP Tent” for gourmet dining and live music, and the chic “Boutique Garden” for fashionable finds. A must-see for horse enthusiasts, the Hampton Classic Horse Show promises a unique spectacle showcasing the beauty and skill of these magnificent animals.


Harborfest  |  Sag Harbor
9/14 – 9/15
HarborFest is a weekend rich in Sag Harbor village’s maritime heritage. Long Wharf buzzes with live music, kids’ activities, delectable food, libations, and a plethora of vendors showcasing Sag Harbor’s cultural and artistic legacy. The annual HarborFest Arts & Crafts Fair at Marine Park boasts over 50 vendors offering handmade art, jewelry, and crafts, while Sunday’s highlight is the renowned HarborFest Clam Chowder Contest. Meanwhile, kids can delight in an expanded Kids’ Zone in Steinbeck Park, featuring pony rides, a petting zoo, educational exhibits, sea-themed crafts, and thrilling performances. Don’t forget to catch the whaleboat races off Windmill Beach, a beloved tradition dating back to the Old Whalers Festival of 1964. Throughout the weekend, enjoy live music performances at various venues across town. Cap off your experience with a visit to the Old Whalers’ Church, offering architectural tours, historic organ demonstrations, and a glimpse into Sag Harbor’s storied past.

East End Seaport Museum’s Maritime Festival  |  Greenport  
9/21 – 9/22 | 10a – 5p
The Maritime Festival, is orchestrated by the East End Seaport Museum and typically unfolds late September. Embracing the region’s rich maritime legacy, the festival presents an eclectic array of activities and attractions suitable for visitors of all ages. With over 100 distinctive vendors, captivating exhibits, and engaging demonstrations showcasing maritime traditions such as tall ship displays, wooden boat building, and knot-tying, attendees are immersed in the area’s seafaring heritage. Alongside opportunities to explore the local lighthouse and savor live music performances and seafood delicacies, nautical-themed events add to the maritime flair. For younger attendees, there are fun-filled activities such as face painting, arts and crafts, and a thrilling pirate treasure hunt. Spectators can also delight in the Merry Merfolk Parade on Saturday and indulge in carousel rides at the Antique Carousel on Front Street, culminating in a memorable celebration that captures the essence of the East End’s culture and history while honoring its maritime roots.

Hallockville Country Fair  |  Riverhead
9/28 | 10a – 5p
The Annual Hallockville Country Fair, a cherished event at the Hallockville Museum Farm and typically takes place in early fall. Highlighting the region’s agricultural heritage, the fair showcases exhibits and demonstrations featuring live farm animals, traditional crafts, and delectable fare from local vendors. Attendees can explore historic farm buildings and delve into the area’s rich history.

A standout feature of the Annual Hallockville Country Fair is the inaugural “Farmers Market,” offering farm-fresh produce, baked goods, preserves, and more from local farmers and artisans. Additionally, family-friendly attractions such as a petting zoo, pony rides, and an antique tractor display add to the fun. Live music performances and classic games like tug-of-war and corn-shucking contests enhance the festive atmosphere.


Oktoberfest  |  Grangebel Park, Downtown Riverhead  
10/5  |  3p – 9p
Put on your dirndl and fasten your lederhosen for the Annual Oktoberfest and Reflextions illumination event! Enjoy live entertainment, engaging contests, and indulge in delicious German-style cuisine from Seaside Grill, accompanied by locally crafted beers. This family-friendly gathering is free to attend, featuring fun-filled activities such as a costume contest and stein-holding contests!

Hamptons International Film Festival 
The Hamptons International Film Festival (HIFF) stands as an annual cornerstone of the East End of Long Island, New York, since its establishment in 1992. Evolving into one of the film industry’s leading events, HIFF showcases an impressive array of independent and international cinema over five days, typically held in October. Featuring diverse films encompassing feature-length narratives, documentaries, and short films, HIFF aims to discover and champion emerging talent within the industry. Furthermore, the festival fosters community engagement through panel discussions, Q&A sessions with filmmakers, and collaborative efforts with local organizations and schools, offering educational opportunities and screenings for students. Alongside screenings, HIFF hosts special events including opening and closing night parties and gala events, while also providing free films and public events, ensuring accessibility for all attendees.

WHB Fall Festival  

Annual Fall Festival  |  Montauk Town Green 
10/13  |  11a – 5p
The much-loved Annual Fall Festival, organized by the Montauk Chamber of Commerce & Visit Montauk features the annual Clam Chowder Contest, a vibrant Farmers Market, engaging children’s activities, live performances by local bands, delectable food options, autumn-themed entertainment, beer and wine offerings, a silent auction, and much more! 

Country Fair  |  Downtown Riverhead  
10/13 | 10a – 5p
The Riverhead Country Fair, held every October, is renowned as one of the largest country fairs in New York State. This beloved event boasts a plethora of attractions including street vendors, an array of food and drinks, thrilling carnival rides, live music, entertaining competitions, and a wealth of additional offerings to ensure a day filled with excitement and fun.

HalloweenFest  |  Downtown Riverhead  
10/19  (rain date 10/26) | 2p – 8p
Calling all Halloween enthusiasts! Every October, Downtown Riverhead transforms into a Halloween haven, with streets adorned by goblins, ghouls, and an abundance of tricks and treats. HalloweenFest  is the perfect opportunity to gather the family, don your costumes, and immerse yourselves in the festivities with coffin races, trick-or-treating, and  lively parade! 


Southampton’s It’s a Wonderful Village 

East Hampton Village Holiday Celebration

Winter Festival WHB 

Montauk Holiday Fair  

Discover additional ways to elevate your East End getaway! Join our newsletter for insider tips. Don’t forget to tag your photos with #EndUpHere on social media to share your adventures throughout Long Island’s East End.

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