A Year of Traditions
Most towns this size have a parade and a fall fair. Maynard's versions come with details you don't find elsewhere. Santa arrives by helicopter. The high school radio station (yes, the high school has a radio station) runs a round-the-clock charity telethon that's older than most of the parents watching it. These events are run by volunteers, chambers, students, and bands, some of them for generations, and they're a good measure of what kind of town this is.
December: Santa Flies In
The first half of December is Maynard's signature stretch: a parade weekend and a student-run telethon that have grown up together over five decades.
The Holiday Parade & Helicopter Santa
Maynard's Holiday Parade has run annually for nearly six decades, and the 2025 edition was the 59th. The parade steps off on an early-December Sunday and winds through downtown along Sudbury, Main, Summer, and Nason Streets, with a Holiday Village set up at Memorial Park. The Maynard Business Alliance's Holiday Stroll and tree lighting take over downtown the evening before, making the first weekend of December a full two-day affair.
The part nobody forgets: Santa arrives by helicopter, circling over downtown before the parade reaches the center of town. For a community of 10,000, the crowd it draws from Maynard and well beyond is far out of proportion to the town's size.
WAVM & the Beacon Santa Telethon
WAVM 91.7 FM has broadcast from Maynard High School since 1973. It's a genuinely student-run radio station, plus local public-access television, in a district of about 1,200 students. It started as an audio-visual club and became one of the school's defining institutions.
Every December since 1978, WAVM students have staged the Beacon Santa Telethon: a live, round-the-clock weekend broadcast of auctions, performances, and on-air dares benefiting the Beacon Santa Fund, which has provided holiday assistance to families across twelve area communities since 1965. The 47th telethon, in December 2025, raised over $45,000, its best total in twenty years.
Spring: The Taste & Pride
Spring brings a restaurant-sampling fundraiser that has been running for more than two decades, and one of the region's few small-town Pride festivals.
Taste of Maynard
The Taste of Maynard is the Maynard Education Foundation's flagship fundraiser, held on a spring Sunday, in recent years at Memorial Park in the center of town. Local restaurants and food businesses set up sampling tables, and proceeds fund MEF's grant program for Maynard's public school teachers, staff, and students.
It's a small-town formula that works: the same downtown restaurants that anchor Main Street donate the food, and the money goes back into classrooms a few blocks away. The event has been running for more than two decades.
Maynard PrideFest
Maynard's Pride Festival is one of the newer entries on the calendar and one of the few small-town Pride events in the area. Held each June at Veterans Memorial Park and along a stretch of Summer Street, the 2026 festival was the third annual: a Sunday afternoon of live music, food, vendors, and a pet parade.
That it became an annual fixture within three years says something about the town. Maynard skews a little younger and more eclectic than most of its neighbors, and the calendar reflects it.
Summer: The Band & the Market
Summer in Maynard runs on two standing appointments: Wednesday evenings at Memorial Park and Saturday mornings beside Mill Pond.
Maynard Community Band
The Maynard Community Band plays free Wednesday-evening concerts at Memorial Park from mid-June through late August, 7:00 to 8:30pm. The programs mix marches, Broadway numbers, film themes, and patriotic standards. The 2026 season is the band's 79th.
Seventy-nine seasons of a volunteer town band is the kind of continuity that has become rare anywhere. Bring a lawn chair; that's the entire price of admission.
Farmers' Market at Mill Pond
The Maynard Farmers' Market has run every summer since 1996. It sets up Saturdays from 9am to 1pm, rain or shine, late June through late September, in the Mill & Main parking lot beside Mill Pond at the corner of Main and Sudbury Streets. The Assabet River Rail Trail passes directly alongside, so a good share of shoppers arrive by bike.
Summer has picked up newer traditions too: outdoor movie nights and Art in the Park, both at Memorial Park.
Fall: The Street Fair, the Porches & the Studios
Early autumn is when Maynard is at its busiest. The street fair and Porchfest share the first weekend of October, the studios open their doors, and the season closes with costumed kids working Main Street.
Maynard Fest
Maynard Fest is an old-fashioned street fair held on an early-October Saturday at Memorial Park and along Nason Street, with more than 120 vendors, live music on multiple stages, food, and family activities. It has been running for over three decades and reliably draws crowds from across the region.
It's the kind of event that benefits from Maynard's compact downtown: everything is within a few walkable blocks, and the local restaurants, the brewery taproom, and the shops all participate rather than compete with it.
Maynard Porchfest
The day after Maynard Fest, Porchfest turns porches, lawns, and driveways across town into stages for a Sunday afternoon of free music. Local musicians and artists perform for whoever wanders by, and the audience drifts from porch to porch on foot and by bike. Together the two events make the first weekend of October a de facto town festival: street fair Saturday, music on the porches Sunday.
Porchfests run entirely on volunteer hosts and volunteer performers. Maynard's deep bench of working musicians is what makes one possible in a town of 10,000.
ArtSpace Open Studios
ArtSpace Maynard, the nonprofit behind the Barbara Erwin Gallery at 15 Nason Street and working studios at 77 Main Street and 9 Nason Street, opens its studios to the public each fall, timed with the town's autumn festivities. Painters, ceramicists, printmakers, jewelers, photographers, and bookbinders show work in the spaces where they make it.
A spring counterpart has grown up alongside it: a town-wide ArtWalk and Open Studios weekend in early May featuring more than 80 artists, plus a holiday sale in December. For a town this size, the density of working artists is one of its most distinctive traits.
Downtown Trick-or-Treats
On the Thursday evening before Halloween, the Assabet Valley Chamber of Commerce and Maynard's downtown businesses host Downtown Trick-or-Treats. Shops along Main and Nason Streets hand out candy to costumed kids from Maynard and the surrounding towns, and the sidewalks fill the way they otherwise only do for the parade.
It's a small tradition, but a telling one. A downtown compact enough to trick-or-treat is the same downtown that makes the street fair, the pub crawl, and the Holiday Stroll work.
And the Rest of the Year
Two more fixtures that don't fit neatly into one season: a November pub crawl that sends veterans to Washington, and a movie house that has anchored Summer Street since 1949.
The Honor Flight Pub Crawl
Each November, American Legion Post 235 runs the Honor Flight Pub Crawl through downtown Maynard's bars and restaurants. The fundraiser, now past its eighth annual edition, benefits Honor Flight New England, a nonprofit that flies WWII, Korea, and Vietnam-era veterans to Washington, D.C. to visit the memorials built in their honor.
The walkable downtown is what makes it work: the whole route covers a few blocks, and the crawl doubles as a tour of Maynard's bar and restaurant scene.
The Fine Arts Theatre
The Fine Arts Theatre at 19 Summer Street has been showing movies since June 29, 1949, when it opened with "The Red Shoes." In the 1950s and 60s it ranked among the highest-grossing Walt Disney houses in the country. Today it's an independently owned three-screen cinema running first-run, art house, foreign, and retro films a block off Main Street.
The building predates the movies entirely; it started as stables in 1897. A 2013–14 renovation brought digital projection, and new local owners took it over during the pandemic. A town of 10,000 with its own art-house cinema is rare. One where you park free out front is rarer.
Dates, routes, and details vary year to year. Check the Town of Maynard, Discover Maynard, and each organizer's site for current schedules. Event histories per the organizers: WAVM (broadcasting since 1973; telethon since 1978), Beacon Santa Fund (est. 1965), Maynard Farmers' Market (est. 1996), Maynard Community Band (79th season, 2026), Maynard Holiday Parade (59th, 2025), Fine Arts Theatre (opened 1949).