16 Can’t Miss Events in Stamford: A Local’s Guide

Stamford, Connecticut is a bustling city filled with events and activities for people of all ages and interests. From food festivals to outdoor concerts, there’s always something going on in this vibrant city. Each year, Stamford hosts a number of annual events for locals to come together and celebrate.

Whether you’ve been living in Stamford all your life, thinking about test driving a new city and renting an apartment, or possibly even relocating and buying a home in Stamford, the annual events in Stamford are not to be missed. They provide a glimpse into the rich culture and history of the city, while also offering a chance to experience some of the best food, music, and entertainment the area has to offer. We asked Stamford residents and local businesses to share their favorite annual event and here’s why they love it.

Luckypawlooza tents
Photo Courtesy of Lucky Dog Refuge

1) Don’t miss the bag sale at The Friends Book Shop

The Friends Book Shop offers a really fun bag sale event twice a year. For $10/bag customers can fill it to the brim with books of their choice. This event occurs in June and October. The Friends Book Shop is located inside the main Ferguson Library downtown as well as in the Harry Bennett branch on Vine Road. They’re always a destination for tourists and locals who love to browse and find something unique to read.

2) Adopt a animal in need at Luckypawlooza

A local favorite is the annual fundraiser called Luckypawlooza, organized by Lucky Dog Refuge and Mill River Park. Proceeds benefit Lucky Dog Refuge and the park. Well-behaved dogs are welcome at the event which features live music, a beer garden, adoptable animals, food trucks, friendly competitions, lure course, silent auction, and more.

October 2022 was the inaugural event which brought in 1500 attendees, 41 sponsors/commercial vendors, 15 non-profits, and 6 contributors to the beer garden. Stamford locals and visitors alike are already looking forward to this year’s event, which is currently scheduled for Saturday, October 14, 2023. 

Dog at Luckypawlooza, an Event in Stamford
Photo courtesy of Lucky Dog Refuge

3) Discover your new favorite restaurant at Stamford Restaurant Week

Stamford Restaurant Week is a fantastic opportunity for local residents to discover new and exciting dining experiences at a fraction of the cost. By choosing to dine at one of the participating restaurants, you’re helping to boost the local economy and ensure that these establishments remain a vital part of the community.

Irina Price, Assistant Property Manager at 75 Tresser shares, “We love Stamford Restaurant week – our residents love to stop by the office and tell us the best restaurant they were able to check out and the great deals that are worth taking advantage of.”

4) Enjoy one of the many shows at Curtain Call

Curtain Call is an award-winning theatre in Stamford which offers an annual free outdoor Shakespeare on the Green program each July, featuring a full scale production of a Shakespearean classic on their own version of the famous Globe Theatre Stage. Year round productions of Broadway musicals, comedies and dramas, as well as concerts, comedy nights and more (indoor) are presented in the Kweskin Theatre and in the Dressing Room Theatre. 

Shakespeare play at Curtain Call

5) Spend a day at HarborFest

“HarborFest is a can’t miss event in Stamford,” says Bob Mazzone VP of Development at SoundWaters, an organization to educate others on protecting and preserving Long Island Sound. “The festival brings Stamford to the harbor for the city’s annual celebration of its historic and thriving waterfront. Thousands of visitors of all ages will flock to the Harbor Point Waterfront to enjoy, historic boat tours of Stamford Harbor, Schooner rides, marine animal touch tanks and education exhibits, kids boat building, mini golf, dockside boat tours and of course, the Aquarion Cardboard Kayak Race for the Mayor’s Trophy. HarborFest is Stamford’s celebration of the Harbor and all its sea shore amenities.” 

6) Spend an afternoon at Mill River Park’s award-winning Carousel Pavilion

“Children of all ages can take a ride on one of the David & Marian Nissen Carousel’s 30 handcrafted animals, from festive horses to more non-traditional options inspired by local wildlife,” says Britt Garth, Senior Communications Manager at Mill River Park. “A springtime visit to the Carousel when the Jaffe Heritage Cherry Grove is in bloom is sure to become a lasting memory. The Pavilion’s whimsical charm also makes it an unforgettable venue for event rentals and parties.”

Carousel at Mill River Park
Photo Courtesy of Mill River Park

7) The 11th Annual Gala Event at the Palace Theatre with Trevor Noah

The Palace Theatre has been around for 96 years and has been a beacon for the performing arts in Stamford ever since,” says Audrey Casinelli, Marketing Coordinator at The Palace Theatre. “As a non-profit theatre, they provide Arts Education programming to under-resourced youths and diverse programming to the community. The Palace Theatre’s 11th Annual Gala Event is returning this year as an in-person event on March 8th with Trevor Noah as our special artist. The Palace Theatre has become an icon in Fairfield County’s arts and culture landscape.”

8) Enjoy live music at the Alive at Five event

“Villa Italia overlooks Mill River Park, and one of our favorite events is Alive at Five, shares Martina Cordero,” shares Marketing Director at Villa Italia Ristorante & Bar. “As music lovers who host live music nights every Tuesday, we look forward to hearing the artists performing at the event every year. Sometimes the artists come in for dinner, and that’s always fun.”

People enjoying a music festival at night.

9) Get your turkey trot on

The Thanksgiving Day Run in Stamford is the perfect way to start your holiday season on the right foot. Whether you’re a seasoned runner or just looking for a fun and healthy way to spend the day, this run has something for everyone. The course is well-organized and provides a scenic route through the streets of Stamford, allowing you to enjoy the beauty of the city while getting some exercise. The festive atmosphere of the run makes it a fun and enjoyable experience with music, cheering crowds, and other runners providing encouragement along the way. Many runners choose to donate to local charities or participate in food drives, helping to make a positive impact on those in need during the holiday season.

10) Savor the flavor of Stamford at the Downtown Food & Wine Festival

The Stamford Downtown Food and Wine Festival is a food lover’s paradise and a fantastic opportunity to sample the best culinary creations from local restaurants. This festival brings together a diverse selection of restaurants and gives attendees the chance to taste their signature dishes and discover new flavors.The festival also features a variety of wine and beverage tastings, allowing you to sample some of the best drinks that the area has to offer. Whether you’re a wine connoisseur or simply enjoy trying new beverages, there is something for everyone at this festival.

Friends cheersing with wine

11) Attend the Stamford Fine Arts & Crafts Show

This show brings together local artists who showcase their unique and one-of-a-kind pieces, including jewelry, pottery, paintings, and more. This is a great way to meet the artists themselves and learn about their creative processes. These talented individuals have a passion for their craft and are more than happy to share their stories and answer your questions. Don’t miss this opportunity to support local artists, find beautiful and unique items, and make a positive impact on the world.

12) Get in the holiday spirit at the Stamford Tree Lighting and Winter Wonderland Festival

The Stamford Tree Lighting and Winter Wonderland Festival brings together the community for a celebration of the holiday season and offers a wealth of fun activities for all ages. From live music and delicious food, to ice-skating and a holiday market, there is something for everyone at this spectacular event. The festive atmosphere is sure to put you in the holiday spirit and create memories that will last a lifetime.

13) Ring in the New Year at the New Year’s Day Parade

This celebratory event is the perfect way to kick off the year on a high note. With its vibrant atmosphere, stunning floats, and heartwarming displays of community spirit, the New Year’s Day Parade is a true celebration of all that is good in the world. Whether you’re looking for a fun family outing, a festive celebration with friends, or simply want to start the year off with a smile, the New Year’s Day Parade has something for everyone. 

Friends holding sparklers on New Year's

14) Experience the world through film at the Stamford International Film Festival

The Stamford International Film Festival is one of the top things to do in Stamford and film event of the year, offering an unparalleled opportunity to immerse yourself in the world of cinema and explore films from around the globe. With its carefully curated selection of feature-length and short films, you’ll be transported to new and exciting worlds, introduced to fresh perspectives, and moved by powerful stories. Whether you’re a film enthusiast, a culture buff, or simply looking for a unique and entertaining experience, the Stamford International Film Festival is not to be missed. 

15) Shop local at the farmers market

The Stamford Farmers Market is a weekly must-visit. With its offerings of locally grown, fresh and juicy produce, homemade baked goods, and artisanal products, you’ll be sure to leave with a bounty of high-quality and delicious items. Support local farmers and artisans as you shop for your weekly groceries and unique, handmade gifts. This market provides an opportunity for you to indulge in the freshest, most delicious food while also supporting this vibrant community.

Fresh veggies at the local Farmers Market

16) Find some goodies at the Stamford Sidewalk Sale

During the Stamford Sidewalk Sale, local stores and vendors set up shop along the sidewalks to sell their goods. The items for sale typically include clothing, accessories, home goods, and more, and are offered at discounted prices. Whether you’re looking to update your wardrobe, redecorate your home, or simply browse for unique and interesting items, the Stamford Sidewalk Sale is the place to be.

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