Spend a relaxing and fun afternoon strolling the Historic Streets in Downtown Canandaigua. Enjoy hand-crafted beverages and tasty small bites at multiple locations. From local brews and wines to memorable mocktails, bring your friends for a passport experience that takes you to multiple stops and enters you into a chance to WIN up to $500 in Downtown Gift Certificates…Discover unique gift shops, galleries, breweries, wineries, and restaurants along the way!

Plaid Friday

Taking the threads of the community and weaving them together to support independent shops on this Friday after Thanksgiving. As an alternative to Black Friday, Plaid Friday encourages individuals to do their holiday shopping with locally owned and independent businesses. Enjoy personalized service and discover one-of-a-kind gifts.

Bring the whole family downtown for a magical holiday celebration as Canandaigua transforms into "Who-ville"! The festive fun centers around the Grinch Village, where you can enjoy themed holiday activities and immersive Whobilation cheer. The highlight of the evening features a special appearance by community leaders and festive characters to officially kick off the holiday season.

• Date: Friday after Thanksgiving

• Time: 3:45 PM – 5:00 PM

• Tree Lighting: At dusk (approx. 4:45 PM) with The Grinch, and friends

• Location: Grinch Village, 111 South Main Street, Canandaigua, NY

• Admission: Free

Stroll through Historic Downtown Canandaigua and discover vibrant local art, live demonstrations, and creative pop-ups as shops and galleries open their doors for a community Art Walk celebrating local talent.

Shop Small is BIG in Canandaigua! When you support your local community, you support your local economy. Shopping with Canandaigua-owned small businesses this holiday season, you'll enjoy friendly service from knowledgeable staff and find quality merchandise and gifts.

Illuminate Canandaigua Light Parade with Santa’s arrival at Commons Park and the Tree-lighting Ceremony all beginning at 6:00 PM.

Kick off the holiday season with a dazzling display of holiday lights as Downtown Canandaigua Illuminates the night. Enjoy a spectacular procession of illuminated floats, fire trucks, antique cars, and local organizations. The parade begins at City Hall bringing Santa, his elves, and loads of holiday cheer. The traditional Tree Lighting Ceremony will immediately follow the parade at the Commons Park. Enjoy caroling, food, and fun as we Light Up Canandaigua!

Experience one of Canandaigua’s most beloved holiday traditions! Tuba Christmas returns to downtown on Saturday, December 5, 2026, bringing the rich, warm sounds of the season to Commons Park.

This free, family-friendly community concert features dozens of local musicians of all ages performing classic holiday carols exclusively on low brass instruments—including tubas, sousaphones, baritones, and euphoniums. It’s the perfect, festive soundtrack to jumpstart your afternoon of holiday shopping and dining on Main Street.

• Want to perform? Tuba and euphonium players of all horn styles and skill levels are invited to participate. Registration and rehearsal take place just prior to the event. Players are encouraged to decorate their instruments and wear bright, festive holiday attire!

• Spectators: Dress warmly, bring your holiday spirit, and gather around the park to sing along to your favorite Christmas carols. FREE to Attend!

Pair Your Day: Keep the festive spirit rolling! After the final notes fade downtown, head down toward the lakeshore to catch the kickoff of the annual Canandaigua Progressive Keg Tree Lighting starting at 5:00 PM.

Kick off the holiday season with the ultimate craft beverage celebration! The annual Canandaigua Keg Tree Lighting is back for Saturday, December 5, 2026. Grab your friends and follow the progressive festive trail across four of Canandaigua's favorite local taprooms as they light up their custom, stacked beer-keg holiday trees.

Each stop along the trail features unique holiday cheer, live music, and special seasonal draft pours. Time your crawl to catch every countdown:

• 5:00 PM – Twisted Rail Brewing Co. (169 Lakeshore Dr) — The holiday crawl officially kicks off lakeside with live tunes.

• 6:30 PM – Other Half Brewing (24 Lakeshore Dr) — Head just down the road for the second lakeside lighting of the night.

• 8:00 PM – Frequentem Brewing Co. (254 S Main St) — The party moves into the downtown historic core to light up the main strip.

• 9:30 PM – Peacemaker Brewing Co. (39 Coach St) — Gather just off Main Street for the grand finale lighting to cap off a festive evening.

Local Event Pairing: Make it a full day of holiday spirit! Before the trail moves downtown, stop by Commons Park to enjoy the classic community favorite Tuba Christmas, featuring festive holiday carols played entirely by local tuba and brass players.

Admission to the trail is free. Cheers to the holidays in Canandaigua!