Every public & political event in and around SD-16 where Jack can show up, shake hands, and earn votes — graded by impact, mapped in/out of district, and click-to-status for the team.
A+ Must-attend. Huge crowds or an endorsement gate.
A High value. Strong voter contact / key constituency.
B Worth a stop. Steady retail or recurring.
C Optional / surrogate-able / out-of-district.
🔵 To Review → ⭐ Priority → ✅ Confirmed → 🟠 Maybe → ⛔ Skip → back.
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In-District one of the 5 SD-16 towns.
Regional outside SD-16 but strategically worth it.
★ On the calendar already booked on Jack's campaign calendar (defaults to ✅ Confirmed).
confirmed likely confirm date — verify "confirm date" items before locking in.
Free Wednesday concerts 7–9 PM on the Town Green all summer + a classic car show each week. The single best recurring retail-politics venue in the district — lawn chairs, families, repeat crowds. Work the rope line weekly.
THE field launch — already locked on Jack's calendar. First organized door-knock of the cycle: turn out every volunteer, capture photo/video for digital, and set the tone for the whole summer canvass program. Confirm the launch site/turf with the field team.
Virtual CTDems training with Vice Chair Jimmy Tickey on building a formal intern pipeline + persuasion conversations. Useful for staff/field given the open Coalitions & Field Manager seat. Already on the campaign calendar.
The summer GOTV backbone already on Jack's calendar — recurring afternoon & evening door-knocking blocks from Jun 22 onward. Build volunteer shifts around these and pair canvass turf with the festivals/markets on this board for same-day doubles.
Jack's endorsement interview with Reproductive Equity Now. Repro rights is a top-three message pillar — strong fit for the purple-district, pro-choice independent voter. Prep talking points; this is an endorsement gate.
Statewide labor convention — delegates vote on candidate ENDORSEMENTS for the 2026 primary & general. Labor's ground game and money follow these endorsements. Highest-leverage non-public event of the summer; get Jack in front of the right locals.
Confirmed host event with Doug Stuke at Señor Pancho's of Prospect (280 Cheshire Rd). Stuke is also the proposed Regency at Prospect host — nurture this relationship; it's a gateway to the Prospect senior & independent network. Bring less-partisan lit per the host's preference.
The CT Democrats' Mobilize hub — trainings, canvasses, candidate caucuses and coordinated 'Organizing Summer' actions post regularly. Subscribe and sweep weekly so the campaign never misses a coordinated event near the district.
Wolcott Summer Concert Series on the Town Green, 6–8 PM (full 2026 band schedule released by the town). Wolcott is core SD-16 turf and historically Sampson-friendly — show up, be seen, soften the margin.
Citywide fireworks from Holy Land USA — huge, diverse Waterbury crowd. Patriotic, non-partisan setting that fits Jack's broad-appeal lane. Walk the gathering areas beforehand; bring lit/swag.
First Tuesday at the Cheshire Senior Center (Jul 7 / Aug 4 / Sep 1 / Oct 6). Where Cheshire's activists and volunteers live. Get on an agenda for a quick candidate address + volunteer ask.
Downtown transforms into an open-air gallery + street fair — 100+ artists, food, live music, big foot traffic. Great for casual voter contact across a wide cross-section of the city.
Weekly Friday market on the Town Green — predictable, low-cost, high-frequency retail. Pairs naturally with Music on the Green season. Confirm 2026 run dates with the town.
Outdoor market by Town Hall — steady neighbor-to-neighbor contact. Good for the candidate or a volunteer table. Confirm 2026 day/time.
Home-town committee meeting that falls inside the party-endorsement window — they're actively interviewing candidates. Lock Jack's relationship + ask about the 'Sea of Flags' visibility program. Core base-building.
Downtown Waterbury's Thursday market pairs with a Rotary summer concert series — easy weekly urban voter contact. Confirm the 2026 CT schedule via Discover Waterbury (don't rely on aggregator listings).
Free Friday-night concert series at Bartlem Park (520 South Main St.). Reliable Cheshire family crowd. Confirm the 2026 lineup/dates with Cheshire Parks & Rec, then slot Jack into 1–2 nights.
Wolcott is a must-organize SD-16 town with no obvious campaign anchor yet. Find the DTC meeting cadence (via CT Dems DTC directory) and get Jack in front of them early. Relationship + volunteer recruitment.
Small town, outsized turnout — the DTC is the fastest route to volunteers and household-level reach. Confirm meeting schedule via the CT Dems DTC directory and schedule a candidate visit.
Classic Southington community festival (Lower Center St. / Sons of Italy). Food, music, multi-generational local crowd — exactly the persuadable moderate / independent universe Jack needs. Confirm exact dates with the Sons of Italy.
Big gearhead crowd at the Southington Drive-In. Skews the blue-collar, less-partisan men Jack is courting. Low-lift handshake stop; pair it with the Italian-American Festival the same weekend.
The area's largest agricultural & family event of the summer — livestock, oxen pulls, crafts, thousands of attendees over 3 days. Marquee in-district opportunity in a town Jack must compete hard for. Consider a booth/table.
Statewide primary date — pivot point from primary to general planning and GOTV. Not an 'attend' event, but every August field decision keys off it. Lock the calendar around it.
Active Dem women's club — strong volunteer & small-dollar base, and a natural ally on Jack's repro-rights and cost-of-living message. Check their calendar for socials/forums to attend or co-host.
The marquee labor political breakfast of the year — electeds, candidates, union leadership all in one room. Strong relationship and earned-visibility play heading into the general. Confirm 2026 date/venue with Council 4.
VW/classic-car meet at the Southington Drive-In, 9 AM–2 PM. Niche but friendly crowd; optional / surrogate-friendly. Good for a quick visibility lap if Jack's already in town.
4th annual — and first-ever TWO-day — downtown celebration; 5,000+ in 2025 and growing. The premier event to reach Waterbury's Puerto Rican & Latino community, a base Jack needs to over-perform with. ⚠ Conflicts with Cheshire–Prospect; consider parade marching unit.
Two-town festival at Bartlem Park — Food-Truck Friday + Saturday on the Great Lawn. Covers TWO district towns (Cheshire + Prospect) in one footprint. ⚠ Same weekend as the Waterbury PR festival — plan split coverage.
THE flagship — two weekends, tens of thousands of attendees, a Southington institution with a parade, carnival, vendors and food. The biggest single voter-contact opportunity in SD-16, four weeks before Election Day. Booth + parade unit + daily presence. Top of the list.
21+ years running on the Prospect Green, with an evening parade. Prospect is a small, high-turnout SD-16 town where face time moves numbers. Confirm exact 2026 date on the town calendar; line up a parade walk.
The League of Women Voters / CT Public typically host nonpartisan candidate forums in the fall. Watch for an SD-16 (Perry vs. Sampson) invite and prep early — earned-media moment in front of high-information voters.