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Events

Group trips, travel meetups, and community gatherings.

May 2026

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1
Sonnenberg Gardens Opens for the Season: 50 Acres of Victorian Gardens in Canandaigua Starting May 1
Wine & Herb Weekend on the Cayuga Lake Wine Trail — May 1–3, 2026
+1 more
2
Kentucky Derby High Tea at Geneva On The Lake — May 2
3
4
5
6
7
Eco-Book Club and Hike at Cumming Nature Center — A Finger Lakes Day Trip Worth Making
8
Rochester Lilac Festival 2026 — Highland Park, May 8-17
Civil War Days at Sonnenberg Gardens: History Comes Alive in Canandaigua
+4 more
9
Orange Wine Vertical Tasting at Atwater Vineyards: Library Wines and a Winemaker Q&A — May 9
Watkins Glen Gorge Trail Opens May 9 for the 2026 Season
+1 more
10
Sip Into Spring: 19 Seneca Lake Wineries, One Pass, Twelve Days
Mother's Day Brunch at Geneva On The Lake — A Finger Lakes Tradition Worth the Drive
+1 more
11
12
13
14
15
Tough Stuff: A New Exhibition at the Corning Museum of Glass Worth the Finger Lakes Drive
16
Classic Euro Car Show and International Festival — A Free Finger Lakes Day Trip, May 16
Sip into Summer — Canandaigua Lake Wine Trail at Inspire Moore Winery, May 16
+4 more
17
Meet Your Local Farmer Fair: Live Music, Chef Demos, and Farm Vendors in Canandaigua — May 17
Sourdough and Wine at Three Brothers Wineries
18
19
Morning Yoga at Hunt Country Vineyards: A Spring Series in the Vineyard
Geneva Music Festival 2026
+1 more
20
21
Jeremy Denk Solo Piano — Geneva Music Festival
22
GlassFest 2026: A Free Weekend in America's Crystal City
23
National Lake Trout Derby on Seneca Lake — May 23-24
Warblers, Wildflowers, and Wine at Montezuma Winery: A Morning in the Finger Lakes That Starts With Binoculars and Ends With a Glass
24
25
26
27
Musical Mixology — Wine, Music, and Community at Linden Social Club
28
Greek Fest Rochester: Four Days of Food, Music, and Culture — May 28-31
29
Pinot Noir Decoded at New York Kitchen: The Science Behind the Heartbreak Grape
Immersive Wine Pairing at Six Eighty Cellars: A Seneca Lake Evening Worth the Drive
30
Fred Hersch Trio — Geneva Music Festival
The Many Faces of Chardonnay at New York Kitchen: A Friday Afternoon in Canandaigua Worth Planning Around
+3 more
31
Local

Morning Yoga at Hunt Country Vineyards: A Spring Series in the Vineyard

Tuesday, May 19, 2026

Hunt Country Vineyards, Branchport, NY

There are worse places to do your Sunday yoga than a vineyard overlooking Keuka Lake. Hunt Country Vineyards hosts weekly sessions with Jan Corning through May 19 — a spring series that gives you a re

Local

Geneva Music Festival 2026

Tuesday, May 19, 2026

Various venues, Geneva, NY

For three weeks in late May and early June, Geneva becomes one of the best reasons to be in the Finger Lakes. The Geneva Music Festival brings piano recitals, chamber ensembles, and jazz to venues acr

Local$40 per concert / Season Pass available

Geneva Music Festival Expands to Four Weeks for 2026: Grammy Winners, Free Pop-Ups, and Wine Pairings

Tuesday, May 19, 2026

Various venues, Geneva, NY

The Geneva Music Festival expands to four weeks for 2026 — Grammy-winning artists across classical, jazz, bluegrass, and Americana. Many performances paired with local winery tastings. Free pop-up con

LocalFree – $40

Jeremy Denk Solo Piano — Geneva Music Festival

Thursday, May 21, 2026 at 7:30 PM

Gearan Center for the Performing Arts – Froelich Hall, Geneva, NY

Jeremy Denk is one of those pianists who makes you think about music differently — his writing about music is as celebrated as his playing, and his concerts tend to reward curiosity. Hearing him in a

RegionalFree

GlassFest 2026: A Free Weekend in America's Crystal City

Friday, May 22, 2026 at All day, three days

Downtown Corning, NY (Market Street / Riverfront Centennial Park)

GlassFest returns to downtown Corning for its annual three-day celebration of glass, craft, and community. More than 100 vendors line Market Street and Riverfront Centennial Park with live glass blowi

Local

National Lake Trout Derby on Seneca Lake — May 23-24

Saturday, May 23, 2026

Seneca Lake, NY

A two-day fishing competition on Seneca Lake with a $7,500 grand prize and multiple category winners. Seneca Lake is one of the top lake trout fisheries in the Northeast.

LocalCheck website for details

Warblers, Wildflowers, and Wine at Montezuma Winery: A Morning in the Finger Lakes That Starts With Binoculars and Ends With a Glass

Saturday, May 23, 2026 at 10:00 AM - 1:00 PM

Montezuma Winery Finger Lakes, 2981 US Route 20, Seneca Falls, NY

Montezuma Winery in Seneca Falls is hosting a morning that pairs guided birding with wine — a walk through the grounds near the Montezuma Wetlands to spot spring warblers and wildflowers, followed by

Local$80

Musical Mixology — Wine, Music, and Community at Linden Social Club

Wednesday, May 27, 2026 at 7:00 PM

Linden Social Club, Geneva, NY

The Geneva Music Festival's most social evening pairs live music with wine and cocktails at the Linden Social Club — a format that invites you to mingle as much as to listen. This is the festival at i

Local

Greek Fest Rochester: Four Days of Food, Music, and Culture — May 28-31

Thursday, May 28, 2026

Greek Orthodox Church, Rochester, NY

Rochester's annual Greek festival returns for four days of traditional food, live music, dancing, and cultural programming at the Annunciation Greek Orthodox Church grounds. One of the city's most pop

Regional$57

Pinot Noir Decoded at New York Kitchen: The Science Behind the Heartbreak Grape

Friday, May 29, 2026 at 6:00 PM - 7:30 PM

New York Kitchen, 800 South Main Street, Canandaigua, NY 14424

New York Kitchen in Canandaigua hosts Pinot Noir Decoded on Thursday, May 29 — a 90-minute deep dive into the grape that winemakers love and fear in equal measure. You'll taste examples that show why

Regional

Immersive Wine Pairing at Six Eighty Cellars: A Seneca Lake Evening Worth the Drive

Friday, May 29, 2026

Six Eighty Cellars, Ovid, NY

Six Eighty Cellars in Ovid is hosting an immersive walk-around wine pairing on Thursday, May 29. Instead of sitting at a bar, you'll move through multiple stations where wines are paired with food in

LocalFree – $40

Fred Hersch Trio — Geneva Music Festival

Saturday, May 30, 2026 at 7:30 PM

Gearan Center for the Performing Arts – Froelich Hall, Geneva, NY

Fred Hersch has spent decades making piano jazz that sounds like conversation — unhurried, attentive, specific. His trio brings that quality to Froelich Hall at the tail end of Memorial Day weekend, a

Regional$58

The Many Faces of Chardonnay at New York Kitchen: A Friday Afternoon in Canandaigua Worth Planning Around

Saturday, May 30, 2026 at 12:00 PM - 1:30 PM

New York Kitchen, 800 South Main Street, Canandaigua, NY 14424

New York Kitchen hosts The Many Faces of Chardonnay on Friday, May 30 — a midday tasting that explores why the same grape can taste like green apple at one winery and butter at the next. Instructor He

RegionalGA ~$97 / VIP ~$131

Finger Lakes Country Music Festival: Lee Brice Headlines in Palmyra — May 30

Saturday, May 30, 2026 at 4:00 PM

Wayne County Fairgrounds, Palmyra, NY

The 5th annual festival at Wayne County Fairgrounds features headliner Lee Brice with Avery Anna. A full day of music plus camping, food trucks, vendors, craft beer, wine slushies, and a classic clamb

Local

Burning Springs Open Gardens Weekend: Bristol Hills Historical Society — May 30-31

Saturday, May 30, 2026 at 12:00 PM

Bristol Hills Historical Society, Canandaigua, NY

Open gardens weekend at the Bristol Hills Historical Society in the Canandaigua area — Saturday and Sunday, noon to 5 PM.

LocalFree

Caledonia Trout Festival 2026: A Small-Town Day Trip Worth the Drive

Saturday, May 30, 2026 at TBD

Main Street and Pioneer Street, Caledonia, NY

Caledonia celebrates its trout heritage with a street festival on Main Street. It's one of those small-town events that feels like stepping into a different pace — food vendors, community spirit, and

Regional

Smith Summer Cabaret Series Opens in Geneva — Live Theater on Seneca Lake

Monday, June 1, 2026

Smith Opera House, 82 Seneca Street, Geneva, NY

The Smith Opera House in Geneva kicks off its summer cabaret series on June 1. This restored 1894 theater is one of the most beautiful performance spaces in the Finger Lakes, and the summer series bri

LocalCheck website for details

Wag Your Tail Along the Cayuga Lake Wine Trail: Two Weeks of Dog-Friendly Wine Tasting

Monday, June 1, 2026 at 10:00 AM - 5:00 PM

Cayuga Lake Wine Trail wineries, Cayuga Lake, NY

The Cayuga Lake Wine Trail is running a two-week dog-friendly tasting event across its member wineries. From June 1 through 14, participating wineries welcome your dog alongside you as you taste your

LocalVaries by venue

Finger Lakes Sweet Treat Trail 2026: Stars, Stripes, and Something Sweet Across Cayuga County

Monday, June 1, 2026

Multiple venues across Cayuga County, NY

The Finger Lakes Sweet Treat Trail is back for 2026 with a Stars, Stripes and Sweet Treats theme. Organized by the Cayuga County Office of Tourism, the trail sends you to a collection of dessert shops

Regional$54

Wine Labels for Dummies at New York Kitchen: A Finger Lakes Evening Worth the Drive

Thursday, June 4, 2026 at 6:00 PM - 7:30 PM

New York Kitchen, 800 South Main Street, Canandaigua, NY 14424

New York Kitchen in Canandaigua hosts Wine Labels for Dummies on Thursday, June 4. If you've ever stood at a wine shop or tasting bar wondering what all those label terms actually mean, this is the ev

Local

Canandaigua in Bloom — Opening of Outdoor Season

Saturday, June 6, 2026 at 9:00 AM

Historic Downtown Canandaigua, 115 Main St., Canandaigua, NY

Every June, Canandaigua's Main Street earns its name. Over 100 hanging flower baskets, earth planters, ground plantings, and window boxes transform the historic downtown into something that rewards a

Local$65

Smokin Summer Kickoff on Seneca Lake

Saturday, June 6, 2026 at 10:00 AM

Seneca Lake Wine Trail, Watkins Glen area, NY

Summer arrives on Seneca Lake with smoke, wine, and the specific pleasure of having absolutely nowhere else to be. The Smokin Summer Kickoff sends you across 15 participating wineries with a souvenir

Regional$65 tasting / $25 designated driver

Smokin' Summer Kickoff: Wine and Food Pairings Across 15 Seneca Lake Wineries

Saturday, June 6, 2026 at 10:00 AM

15 wineries across Seneca Lake Wine Trail, Geneva NY region

Fifteen Seneca Lake wineries open their doors for the Smokin' Summer Kickoff — two days of wine paired with food at every stop, the kind of weekend that reminds you why this region keeps pulling peopl

Local

Keuka Lake Gravel Classic 2026: Ride Through the Finger Lakes Wine Country

Sunday, June 7, 2026

Hammondsport, NY

The Keuka Lake Gravel Classic brings gravel cyclists to Hammondsport for a ride through the vineyard roads and rolling farmland that make the Finger Lakes one of the best cycling regions in the Northe

Local$0-$40

Eighth Blackbird at Geneva Music Festival: Grammy-Winning Chamber Ensemble on Seneca Lake

Thursday, June 11, 2026 at 7:30 PM

Gearan Center for the Performing Arts, Froelich Hall, Hobart & William Smith Colleges, Geneva NY

Six-time Grammy-winning contemporary chamber ensemble Eighth Blackbird performs at Geneva Music Festival. This is world-class musicianship in a Finger Lakes college town — the kind of evening that mak

Local

Freedom Festival 2026: America 250 in Bristol Hills

Saturday, June 13, 2026

Bristol Hills Historical Society, 6751 County Road 32, Canandaigua, NY

America turns 250 in 2026, and the Finger Lakes has a few things to say about it. The Freedom Festival in Bristol Hills brings Revolutionary War reenactors, pioneer craftspeople, vintage games, and hi

LocalFree – $40

Mark & Maggie O'Connor Close the Geneva Music Festival at Geneva On The Lake

Sunday, June 14, 2026 at 4:00 PM

Geneva On The Lake, Geneva, NY

The Geneva Music Festival ends its 2026 season the right way: a Sunday afternoon concert with Mark and Maggie O'Connor at Geneva On The Lake, a graceful historic resort sitting above Seneca Lake. The

RegionalFree outdoor stages; ticketed club shows

Rochester Jazz Fest 2026: Nine Days of Music Worth Planning a Trip Around

Friday, June 19, 2026 at All day / evening

East End / Parcel 5, Rochester NY

The Rochester International Jazz Festival runs nine days in late June and is one of the best-kept secrets in American music festivals. Free outdoor stages at Parcel 5, intimate club shows within walki

LocalCheck website — features $5 draft beers and whiskey pairings

Raise A Glass To Dad Weekend at Montezuma Winery: Whiskey, Jerky, and Draft Beers on Father's Day Weekend

Friday, June 19, 2026 at 9:00 AM - 6:00 PM

Montezuma Winery Finger Lakes, 2981 US Route 20, Seneca Falls, NY

Montezuma Winery is running a four-day Father's Day celebration with Hidden Marsh whiskey paired with beef jerky and five-dollar draft beers. It is the kind of low-key, no-reservation outing that actu

Local

Watkins Glen Waterfront Festival and Cardboard Boat Regatta — June 20

Saturday, June 20, 2026

Watkins Glen, NY (Seneca Lake waterfront)

Watkins Glen hosts its annual Waterfront Festival on Seneca Lake, headlined by the Cardboard Boat Regatta — where teams race boats made entirely of cardboard and tape across the water. Most of them si

Local

20th Annual Father's Day Car Show at Sonnenberg Gardens

Sunday, June 21, 2026 at 10:00 AM

Sonnenberg Gardens & Mansion State Historic Park, 250 Gibson St, Canandaigua, NY

Sonnenberg Gardens turns 20 for its Father's Day Car Show this June, filling the mansion's shaded south lawn with timeless classic cars. It is the kind of Father's Day that doubles as a reason to be o

LocalCheck website — fundraiser event

Mumus and Mimosas: A Summer Evening at Montezuma Winery for Ovarian Cancer Awareness

Friday, June 26, 2026 at 6:00 PM - 9:00 PM

Montezuma Winery Finger Lakes, 2981 US Route 20, Seneca Falls, NY

Montezuma Winery is hosting Mumus and Mimosas — an evening of welcome mimosas, DJ music, and fundraising for Hope for Heather ovarian cancer awareness. Wear your favorite mumu and settle in for a summ

Local

Arts at the Gardens (25th Edition) at Sonnenberg

Saturday, June 27, 2026 at 10:00 AM

Sonnenberg Gardens, 250 Gibson St., Canandaigua, NY

For 25 years, artists have been setting up their work in the Victorian gardens at Sonnenberg — and it shows. Arts at the Gardens brings painters, photographers, jewelers, and potters together across t

Local

FLXcursion 2026: The Finger Lakes Riesling Conference That Puts Geneva on the World Wine Map

Saturday, June 27, 2026

Geneva, NY

FLXcursion 2026 brings winemakers and enthusiasts from Riesling regions around the world to Geneva, New York for three days of seminars, tastings, wine dinners, and vineyard tours.

Local$50

Run the Vineyards: 5K Through Sheldrake Point Winery

Sunday, June 28, 2026 at 9:00 AM

Sheldrake Point Winery, Ovid, NY

This is a 5K where the finish line leads directly to a wine glass. The course winds through 200 acres of working vines along the western edge of Cayuga Lake — chip-timed, unhurried in spirit, and endi

Regional

GrassRoots Festival 2026: Four Days of Music, Dance, and Community in Trumansburg

Thursday, July 16, 2026

Trumansburg Fairgrounds, Trumansburg, NY

The GrassRoots Festival of Music and Dance returns to Trumansburg for its 34th year this July. Four days, four stages, 70-plus bands — and the kind of unhurried community energy that makes you forget

LocalFree gate / $10 parking

Ontario County Fair 2026: Five Days of the Real Finger Lakes

Tuesday, July 21, 2026 at 10:00 AM

Ontario County Fairgrounds, 2820 Co Rd 10, Canandaigua NY

The Ontario County Fair hits 183 years — five days of 4-H shows, livestock, midway rides, demolition derby, and live music at the Canandaigua fairgrounds. This is the Finger Lakes at its most genuine.

LocalVaries by performance

Skaneateles Festival 2026: World-Class Chamber Music by the Lake This Summer

Saturday, August 1, 2026

First United Methodist Church and village venues, Skaneateles, NY

Every August, Skaneateles becomes one of the most quietly extraordinary places in the Finger Lakes. The Skaneateles Festival brings world-class chamber musicians to intimate village venues — the kind

Local

Gone to the Dogs: Bring Your Dog to the Seneca Lake Wine Trail This August

Friday, August 21, 2026 at 10:00 AM

Seneca Lake Wine Trail member wineries, Watkins Glen area, NY

The Seneca Lake Wine Trail turns dog-friendly for a full week every August, and Gone to the Dogs is the event that makes it official. With a tasting pass in hand, you and your leashed companion move f

RegionalVaries by race

Wineglass Marathon 2026: Run Through the Finger Lakes This October

Sunday, October 4, 2026 at 7:45 AM

Bath to Corning, NY

This October, one of the most beloved fall marathons in the Northeast returns for its 45th anniversary. The Wineglass Marathon runs point-to-point from Bath through the Finger Lakes valley into Cornin

RegionalFree (most activities)

Days of Incandescence: Corning's October Night Walk Through Glass and History

Monday, October 26, 2026 at 4:00 PM – 8:00 PM

Corning Historic District, Centennial Park, Centerway Square, Corning NY

Corning's historic district comes alive for Days of Incandescence — an October evening walking event that weaves together the city's glass heritage, Thomas Edison's history, and a touch of the superna

Local$35–$120

Deck the Halls on the Seneca Lake Wine Trail: A Holiday Weekend Worth the Drive

Friday, November 20, 2026 at 10:00 AM

Seneca Lake Wine Trail member wineries, Watkins Glen area, NY

Before the holiday month gets away from you, the Seneca Lake Wine Trail spends a weekend in late November dressed for the season. Deck the Halls sends you winery to winery on a self-guided tour throug

Local$35–$120

December Deck the Halls: Seneca Lake Wine Trail Holiday Weekend — December 4-6

Friday, December 4, 2026 at 10:00 AM

Seneca Lake Wine Trail member wineries, Watkins Glen area, NY

The Seneca Lake Wine Trail does the holidays properly, and the December version of Deck the Halls gives you the whole experience: decorated tasting rooms, winter pours, and the kind of unhurried winer

Past Events (34)
Local$75

Sourdough and Wine at Three Brothers Wineries

Sunday, May 17, 2026

Three Brothers Wineries, Penn Yan, NY

Some winery weekends call for more than just tasting. The sourdough baking class at Three Brothers Wineries puts you in the kitchen at the Knead and Seed Bakery — hands in dough, starter kit to take h

Local

Meet Your Local Farmer Fair: Live Music, Chef Demos, and Farm Vendors in Canandaigua — May 17

Sunday, May 17, 2026 at 11:00 AM

New York Kitchen, Canandaigua, NY

A farm-to-table fair at New York Kitchen in Canandaigua — live music, chef demonstrations using local ingredients, and vendors from area farms and beverage producers.

Local

Corvette: Thunder in the Glen — Watkins Glen International

Saturday, May 16, 2026

Watkins Glen International, Watkins Glen, NY

Watkins Glen International has seen some of the most important motorsport moments in American history. For one May weekend, it becomes a showcase for one of the most iconic American cars ever built —

Local

International Festival and Euro Vintage Car Celebration in Canandaigua — May 16

Saturday, May 16, 2026

Canandaigua Downtown Shopping District, Canandaigua, NY

A cultural festival combined with a European vintage car show takes over downtown Canandaigua on May 16 — international food, culture, and classic European automobiles on one of the Finger Lakes' pret

Regional$40 taster / $10 companion

Sip Into Summer: All Nine Canandaigua Lake Wineries in One Afternoon

Saturday, May 16, 2026 at 12:00 PM

Inspire Moore Winery, 197 North Main Street, Naples, NY 14512

All nine wineries from the Canandaigua Lake Wine Trail gather at Inspire Moore Winery for one afternoon of tastings, live music, and the kind of low-key festival that makes the Finger Lakes feel perso

Local

Corvette: Thunder in the Glen — A Car Show Worth the Finger Lakes Drive

Saturday, May 16, 2026

Watkins Glen International, 2790 County Route 16, Watkins Glen, NY

Watkins Glen International hosts Corvette: Thunder in the Glen, bringing Corvette enthusiasts from across the Northeast to the Finger Lakes for a weekend of car shows, track time, and the kind of shar

Local$35 taster / $15 companion

Sip into Summer — Canandaigua Lake Wine Trail at Inspire Moore Winery, May 16

Saturday, May 16, 2026 at 12:00 PM

Inspire Moore Winery, Naples, NY

The Canandaigua Lake Wine Trail kicks off its spring season on May 16 at Inspire Moore Winery in Naples — and they're bringing all 9 trail wineries together in one spot. Add live music from Big Blue H

LocalFree

Classic Euro Car Show and International Festival — A Free Finger Lakes Day Trip, May 16

Saturday, May 16, 2026

Canandaigua, NY

Canandaigua hosts a Classic Euro Car Show alongside an International Festival — European automobiles on display in one of the prettiest lakeside towns in the Finger Lakes. Free admission, outdoor sett

Local

Tough Stuff: A New Exhibition at the Corning Museum of Glass Worth the Finger Lakes Drive

Friday, May 15, 2026

Corning Museum of Glass, Corning, NY

The Corning Museum of Glass opens Tough Stuff: Women in the American Glass Studio, a new exhibition spotlighting the women who broke into — and helped define — the American studio glass movement. If y

Local$50

Sip Into Spring: Seneca Lake Wine Trail Tasting Pass — May 10–21, 2026

Sunday, May 10, 2026

Seneca Lake Wine Trail, Watkins Glen, NY

The Seneca Lake Wine Trail's Sip Into Spring pass gives you access to tastings at 17 wineries across 12 days — May 10 through 21. One digital pass, no fixed schedule, go at your own pace. With the lar

Local

Mother's Day Brunch at Geneva On The Lake — A Finger Lakes Tradition Worth the Drive

Sunday, May 10, 2026 at 10:00 AM - 4:00 PM

Geneva On The Lake, Geneva, NY

Mother's Day brunch at Geneva On The Lake — one of the Finger Lakes region's most scenic and elegant dining settings for the holiday.

Local$50

Sip Into Spring: 19 Seneca Lake Wineries, One Pass, Twelve Days

Sunday, May 10, 2026 at 10:00 AM

Seneca Lake Wine Trail, Seneca Lake NY

Spring arrives on Seneca Lake the way it should — with a glass in your hand and nowhere to rush. The Sip Into Spring Tasting Pass opens 19 wineries across the trail for twelve unhurried days.

Local

Forest Bathing in Naples, NY — Finger Lakes Wellness Walk

Saturday, May 9, 2026

Naples, NY

A guided forest bathing experience in Naples — slow, sensory immersion in the wooded hills of the southern Finger Lakes.

Local$10 per vehicle

Watkins Glen Gorge Trail Opens May 9 for the 2026 Season

Saturday, May 9, 2026 at Dawn

Watkins Glen State Park, Watkins Glen, NY

After a winter closure, the Watkins Glen gorge opens its doors tomorrow - and the first weeks of the season are quietly the best time to go. Snowmelt pushes the 19 waterfalls to their fullest, the cro

Local

Orange Wine Vertical Tasting at Atwater Vineyards: Library Wines and a Winemaker Q&A — May 9

Saturday, May 9, 2026 at 6:30 PM - 8:00 PM

Atwater Vineyards, 5055 State Route 414, Burdett, NY

Orange wine is having a moment nationally — and Atwater Vineyards is ahead of the curve with a vertical tasting of four exclusive library skin-fermented wines led by Head Winemaker Wes Andrew. Cheese

RegionalVaries — see theglen.com

NASCAR Comes to Watkins Glen in May for the First Time — Triple-Header Weekend, May 8-10

Friday, May 8, 2026

Watkins Glen International, Watkins Glen, NY

NASCAR moved the Watkins Glen Cup Series race from August to May 8–10 for the first time ever. A triple-header weekend: CRAFTSMAN Truck Series on Friday, O'Reilly Auto Parts Mission 200 on Saturday, a

RegionalVaries by ticket

NASCAR Returns to Watkins Glen: Cup Series on the Finger Lakes Road Course

Friday, May 8, 2026

Watkins Glen International, 2790 County Route 16, Watkins Glen, NY

NASCAR comes to the Finger Lakes for the Go Bowling at The Glen weekend — Cup Series, Truck Series, and ARCA all on the 2.45-mile road course that makes Watkins Glen one of the most anticipated stops

Local

Ravi Coltrane at The Smith Opera House — A Jazz Night Worth the Finger Lakes Drive

Friday, May 8, 2026 at 8:00 PM

The Smith Opera House, 82 Seneca Street, Geneva, NY

The Smith Opera House in Geneva opens its stage to Ravi Coltrane — Grammy-nominated saxophonist and son of John Coltrane — for an evening of contemporary jazz that is genuinely worth building a trip a

Regional$56

NY Cider Week at New York Kitchen: A Finger Lakes Evening Worth the Drive

Friday, May 8, 2026 at 6:00 PM – 7:30 PM

New York Kitchen, 800 South Main Street, Canandaigua NY 14424

New York Kitchen hosts a guided hard cider tasting to celebrate NY State Cider Week, featuring local Finger Lakes producers. Expect to explore cider styles, apple varietals, and food pairings — the sa

Local$10/$5/Free (tiered)

Civil War Days at Sonnenberg Gardens: History Comes Alive in Canandaigua

Friday, May 8, 2026 at 9:30 AM - 4:30 PM

Sonnenberg Gardens, 250 Gibson St, Canandaigua NY

Civil War Days returns to Sonnenberg Gardens — reenactors, period demonstrations, and living history on the grounds of Canandaigua's Gilded Age estate. Part of America 250 programming.

LocalFree (individual events may vary)

Rochester Lilac Festival 2026 — Highland Park, May 8-17

Friday, May 8, 2026

Highland Park, Rochester, NY

One of the largest free outdoor festivals in the Northeast happens every May in Rochester — and the 128th annual Lilac Festival is reason enough to plan a trip. Ten days at Highland Park, home to the

Local

Eco-Book Club and Hike at Cumming Nature Center — A Finger Lakes Day Trip Worth Making

Thursday, May 7, 2026

Cumming Nature Center, Naples, NY

There are book clubs. And then there is this. The Eco-Book Club at the [Cumming Nature Center](https://www.rmsc.org/CummingNatureCenter) in Naples, NY meets on a trail — discuss an ecology-focused boo

Local

Kentucky Derby High Tea at Geneva On The Lake — May 2

Saturday, May 2, 2026 at 2:00 PM

Geneva On The Lake, Geneva, NY

Geneva On The Lake hosts a Derby Day afternoon tea on May 2 with two seatings. Traditional Derby Day foods in one of the region's most elegant lakeside settings.

LocalFree with non-perishable food donation

Opening Weekend at Long Acre Farms: Free Admission Weekend in Macedon — May 1-3

Friday, May 1, 2026 at 10:00 AM - 8:00 PM

Long Acre Farms, 1342 Eddy Road, Macedon, NY

Long Acre Farms kicks off its 2026 season with a generous deal — free admission to the Back 40 play area all weekend in exchange for a non-perishable food donation for local food pantries. One donatio

Local$65 single / $95 couples

Wine & Herb Weekend on the Cayuga Lake Wine Trail — May 1–3, 2026

Friday, May 1, 2026

Cayuga Lake Wine Trail, Seneca Falls, NY

The Cayuga Lake Wine Trail's Wine & Herb Weekend runs May 1–3 — your ticket gets you into all 10 participating wineries across the weekend, each pairing their wines with herb-inspired food. It's a str

LocalAdmission required — see sonnenberg.org

Sonnenberg Gardens Opens for the Season: 50 Acres of Victorian Gardens in Canandaigua Starting May 1

Friday, May 1, 2026 at 9:30 AM

Sonnenberg Gardens & Mansion State Historic Park, Canandaigua, NY

Fifty acres of Victorian gardens and a 40-room Queen Anne mansion open for the season on May 1 in Canandaigua. Nine internationally-inspired themed gardens plus one of the few remaining Lord & Burnham

Local$10 adults / $5 ages 4-16 / Free under 3

Orchid Show and Plein Air Showcase at Sonnenberg Gardens This Weekend — April 25-26

Saturday, April 25, 2026 at 10:00 AM - 5:00 PM

Sonnenberg Gardens & Mansion State Historic Park, Canandaigua, NY

One of the first events at Sonnenberg before the full seasonal opening May 1 — orchid displays in the historic Lord & Burnham greenhouse alongside plein air painting demonstrations across the 50-acre

Local

Warblers, Wildflowers and Wine: A Spring Day Trip to Keuka Lake

Saturday, April 25, 2026

Branchport, NY

A nature-focused spring outing combining birdwatching for spring warblers, wildflower walks, and wine tasting in the Keuka Lake area on April 25.

Regional

Warblers, Wildflowers and Wine: A Spring Nature Walk at Hunt Country Vineyards

Saturday, April 25, 2026

Hunt Country Vineyards, Branchport NY

The guided nature walk through Hunt Country Vineyards is one of the better ways to spend a spring Saturday in the Finger Lakes — spring warblers moving through, wildflowers at peak bloom, and wine tas

Local

Sips and Succulents: A New Spring Event on the Keuka Lake Wine Trail — April 24-25

Friday, April 24, 2026

Keuka Lake Wine Trail, Penn Yan, NY

Brand new for 2026 — Sips and Succulents is the Keuka Lake Wine Trail's first-ever spring event. Ticket holders visit six participating wineries for wine samples paired with seasonal small bites, and

Local

Wine and Herb on Cayuga Lake: Spring Pairings Along the Trail

Friday, April 24, 2026 at 10:00 AM

Cayuga Wine Trail, Cayuga Lake NY

Cayuga Lake wineries are pairing their wines with fresh herb-driven dishes this spring. Wine and Herb runs April 24 through May 3, giving you ten days to find your favorite combination.

Regional

Wine and Plant-Based Cheese Tasting: A New Finger Lakes Pairing Experience

Sunday, April 19, 2026

Himrod, NY

Something new is showing up in Finger Lakes tasting rooms this spring — plant-based cheese pairings alongside the region's signature wines. Today's event in Himrod puts a reserve Riesling next to oat-

LocalFree admission and parking

The Windmill Farm and Craft Market Opens for the Season — April 18

Saturday, April 18, 2026 at 8:00 AM - 4:30 PM

The Windmill Farm & Craft Market, Penn Yan, NY

The Windmill Farm and Craft Market opens for its 2026 season tomorrow — the classic Finger Lakes rite of spring. Over 40 acres, 175+ vendors, fresh produce, flowers, local wineries, craft food, and li

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Wine and Cheese Weekend on the Seneca Lake Wine Trail — April 17-19

Friday, April 17, 2026

Seneca Lake Wine Trail, Watkins Glen, NY

The Seneca Lake Wine Trail kicks off its 2026 spring season this weekend with Wine and Cheese — a self-guided tasting event across participating wineries. Go at your own pace across three days. The fi

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