Watertown's Faire on the Square

Join us on Saturday, September 19, 2026, from 12pm to 5pm for Watertown’s beloved annual community celebration, Faire on the Square! Head over to Saltonstall Park, located behind City Hall, for an afternoon filled with FREE family fun and opportunities to connect with your neighbors. Over 100 vendors will be showcasing their products and services, and activities and entertainment will be happening throughout the day, including the "Kid's Adventure Zone" and a bake-off competition. Enjoy food, music, games, and surprises spread across the grounds—who knows what fun you’ll discover? NEW THIS YEAR: Make your way to the Oktoberfest Biergarten hosted by Mighty Squirrel Brewing and enjoy a selection of your favorite craft brews! Vendor registration closes August 28, 2026. Spots are limited! Stay tuned for more updates! <a href="http://www.faireonthesquare.com/?fbclid=IwcGRvZgFleHRuA2FlbQIxMABicmlkETE2anhBbWtsbDNpYjNrekJHc3J0YwZhcHBfaWQQMjIyMDM5MTc4ODIwMDg5MgABHsOcTAGlO7xSlXic6ia4ewp_024BhmRyOLtQWYwDjZMJoFhA5k_-Kywy4rtl_aem_oJ70wNl3q6h-RZ58adrAuw">www.faireonthesquare.com</a>

Saltonstall Park

Watertown Wheels: Classic Car Show

Watertown Wheels 3rd Annual Classic Car Show Sunday, August 2, 2026 | 10:00am - 2:00pm Commander's Mansion 440 Talcott Avenue, Watertown, MA 02472 ​What better way to spend a summer weekend than at a classic car show? Join us for the 3rd Annual Watertown Wheels Classic Car Show—a fun, family‑friendly day featuring an exciting lineup of antique and vintage cars, great food, music, and raffles. This event is free to attend and open to the public.   Fill-A-Truck Food Drive This year, we're proud to partner with the Watertown Food Pantry. All attendees are encouraged to bring non‑perishable food items to donate. Let’s fill the truck and help support our neighbors in need! ​ Car Entries Car owners interested in showing a vehicle are invited to arrive after 9am on the day of the event for on‑site registration. The entry fee is $10 per car, and a portion of the proceeds will benefit the Watertown Food Pantry. Award trophies will be presented for Best in Show. We look forward to seeing you there!

Commander's Mansion

Watertown POPS: Patriotic Lightshow

Watertown POPS: Patriotic Lightshow Wednesday, July 1, 2026 • 8:45pm Saltonstall Park, 149 Main St., Watertown, MA 02472 The United States is turning 250 years old, and that’s the perfect reason to POP off and celebrate! ​ The Watertown City Events Team is proud to present Watertown POPS: A Patriotic Lightshow and Evening of Popping Fun, the grand finale of Watertown’s Independence Day Celebrations. After a full day of activities at Saltonstall Park, wrap up your night and kick off your Fourth of July weekend with our patriotic lightshow beginning at 8:45 PM. Enjoy a live DJ, food trucks, and free Culture Pop Soda (while supplies last) during the show. Bring a blanket or lawn chair and arrive early to secure a great viewing spot. The lightshow is free and open to the public. All are welcome! Below is the full schedule for Watertown’s Independence Day Celebration. ​​​ ​   Watertown's Independence Day Celebration Full Schedule • Wednesday, July 1, 2026 ​Saltonstall Park, 149 Main St., Watertown, MA 02472  ​​​​ 2:30–6:00 PM — <a href="https://www.livewellwatertown.org/farmers-market/">Watertown Farmers’ Market</a> Kick off the holiday with fresh produce, local food, artisan goods, and live music at the weekly Farmers’ Market. The Market supports local agriculture and small businesses while promoting healthy, sustainable living for the whole community. Cash, credit cards (for most vendors), SNAP, HIP, and Farmers' Market Nutrition Coupons are accepted. 6:30–8:00 PM — <a href="https://www.watertown-ma.gov/761/Summer-Concert-Series">Summer Concert Series: Sound Bridges</a> The Summer Concert Series opens with Sound Bridges, an award‑winning NYC‑based global music ensemble. Blending West African rhythms with jazz, blues, and groove-driven styles, they deliver high‑energy, feel‑good performances that get audiences moving and connecting. Bring a blanket or chair. 8:45 PM — <a href="https://www.commandersmansion.com/cityevents/watertownpops">Watertown POPS Patriotic Lightshow</a> End the evening with a dazzling patriotic lightshow set to music. Enjoy a live DJ, food trucks, and free Culture Pop Soda (while supplies last). Bring a blanket or chair and get ready to light up the night as we celebrate 250 years of the United States.

Tipsy Tea Party: Drag Brunch

Tipsy Tea Party 2026: "Drag me to the Disco!" Sunday, June 28, 2026 | 11:30am - 2:00pm Commander's Mansion, 440 Talcott Avenue, Watertown, MA 02472 Pride Month is around the corner, and that means the Tipsy Tea is back!&nbsp;🌈✨This year's theme is "Drag me to the disco!" ​ Join the City Events Team, the Mosesian Center for the Arts, and the Friends of the COA for a festive gathering featuring delicious brunch bites, a cash bar, and fabulous drag entertainment in celebration of Pride. Check out our amazing line-up of performers below! Performances featuring:<ul><li>Stabitha Christie <a href="https://www.instagram.com/stabithakills/">@stabithakills</a> </li><li>Slick O'Connell <a href="https://www.instagram.com/slickoconnell/">@slickoconnell</a> </li><li>Dahlia Strack <a href="https://www.instagram.com/dahliastrack/">@dahliastrack</a> </li><li>Wilhelmina Ladesse <a href="https://www.instagram.com/wilhelminaladesse/">@wilhelminaladesse</a> </li><li>Izzy Ready <a href="https://www.instagram.com/izzyready_/">@izzyready_</a> </li></ul>Dress code: Dress in your best tea attire. There will be a "Purse First" prize for best dressed guest! Tickets are $40 and go on sale Friday, May 1, 2026. This event is 21+.

Poppy Social: Open House & Wreath-Laying Ceremony

Poppy Social:&nbsp;Open House &amp; Wreath-Laying Ceremony Friday, May 22, 2026 | 10:00am - 12:00pm Commander's Mansion, 440 Talcott Avenue, Watertown, MA 02472 We invite all Watertown Veterans—and all members of the community—to join us for the annual Poppy Social. This gathering commemorates Memorial Day and features a meaningful wreath-laying ceremony to honor and remember our fallen Veterans. The Watertown Veterans' Services Department and the City Events Team will host an Open House at the historic Commander's Mansion, located in the Arsenal on the Charles. Guests are welcome to enjoy light refreshments and take part in guided tours of the residence. Please plan to arrive by 10:30am for the Honor and Color Guard wreath-laying ceremony with the Watertown Police and Fire Departments. This event is free and open to the public. All are welcome.

S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

Best places to go in Boston? Things to do? Places to eat?

Questions & answers about things to do in Boston

Recs 💬

Community recs 💬

S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

Hot and new things to do in Boston

Hot & new

Hot & new 🔥

S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

This wknd

This weekend for you

S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

Roundups ⭐️

Curated by Joyraft ⭐️

S28: calendar experiences

This week in Boston

This week in Boston 📆

This week 📆

S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

The newest events happening in and around Boston

The newest events on Joyraft

Just added

Just added to Joyraft

S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

Top 20 on Joyraft

S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

The hottest events happening in Boston

Trending events on Joyraft

Trending 📈

S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

Boston Bars and Restaurants: Events and Openings

Food & drink experiences in Boston

Food & drink experiences 

City of Watertown, MA - Events Team

Where

watertowneventsteam

Experiences

Watertown's Faire on the Square

Watertown Wheels: Classic Car Show

Watertown POPS: Patriotic Lightshow

Tipsy Tea Party: Drag Brunch

Poppy Social: Open House & Wreath-Laying Ceremony