Can’t-Miss Fall Live Music Finds

Summer’s coming to an end, but that doesn’t mean the music has to. Our friends at River Towns Music Group have put together some can’t-miss, live music experiences coming up this fall in the tristate area. There’s plenty to choose from for music lovers, families or anyone who just likes a great reason to party.   


Sound on Sound

Seaside Park, 1 Barnum Dyke, Bridgeport, CT 06604

Saturday, September 24 – Sunday, September 25


A brand new, two-day music festival in Bridgeport, CT, featuring a stacked lineup and an equally impressive list of upscale amenities to satisfy even the most aficionado of aficionados.


Saturday: The Lumineers, Stevie Nicks, Father John Misty, Ziggy Marley, Caamp, Band of Horses, Zach Bryan, Jenny Lewis, Trampled by Turtles, Geese, the Cameroons, Drew Angus

Sunday: Dave Matthews and Tim Reynolds, Brandi Carlile, The National, The Roots, Gary Clark Jr, The Head and the Heart, Noah Kahan, Spin Doctors, Jade Bird, The Main Squeeze, Trousdale, Charley

Why Go?


If you like music and have been living on earth for the past couple of decades, you’ve probably heard of a bunch of these bands. This is one place you can catch this exact mix of long-adored and newly-minted heavy hitters. Secondly, this festival is brought to you by the same people that bring you Governors Ball, a company called Founders Entertainment. These guys know how to build a music festival.


Are you pretty sure you’re not into musical festivals anymore (or never really were)? This might be the festival for you. With Sound on Sound, Founders Entertainment set out to craft an elevated festival experience that caters to a more discerning, sophisticated audience. With decades of research and experience under their belts, they’ve thought of all the amenities people in their 30s, 40s, 50s and beyond could want. As Tom Russell, Co-Founder and Partner of Founders Entertainment, told us, “If you’re a music lover who also enjoys the finer things in life, Sound on Sound is the festival for you.”


Everybody gets thirsty at a music festival. Luckily this one has plenty to offer. Fancy yourself a wine connoisseur? Check out SOS’s impressively expansive Seaside Wine Grove, where you can get a great chardonnay or even enjoy some orange varietals and enjoy it in the comfort of a massive tent decked out with ample seating and elevated decor. Love a good cocktail? Let the mixologists at Shaken and Stirred whip up something special for you. Want a beer and don’t want to miss a game? Head to the Craft Beer & Sports Hall, where you can enjoy a microbrew and not miss a single inning.


Got kids? Cool, kids five and younger are free with a ticket-holding adult. Strollers are allowed too. To keep your kids entertained, SOS will have Ramblin’ Dan’s Freewheelin’ Band play several sets per day at the family area. There will be bubble machines and other festival staples. There’s also a playground built into the footprint of the festival, and there are permanent restrooms with changing stations conveniently located in the family zone. Yay, no port-a-potty adventures with your toddler!


With three miles of shoreline on the Long Island Sound, Seaside Park is a waterfront oasis designed by Frederick Law Olmstead, the same landscape architect who designed Central Park and Golden Gate Park. Conveniently, Seaside Park’s about an hour away from most of the river towns.


Expect nothing short of the best of everything at this festival. Tom Russell finished our interview by saying, “We’re building Sound on Sound with a 50-year plan. So, for year one, we have no other option but to nail it.” And you better believe they will.


1-day GA starting at $169

2-day GA starting at $279

Pound Ridge Harvest Festival

Pound Ridge Town Park – Westchester, Ave, Pound Ridge, NY 10576

Saturday, October 1 from 1pm-6pm


A free, Octoberfest-inspired day of music, beer, wine, food and family entertainment.


Blues Traveler headlines with support from Battle of the Bands winners Badger Scratch and Platinum Moon.

Why Go?


Seeing Blues Traveler is awesome. Seeing Blues Traveler for free is epic. Pound Ridge Harvest Festival is no stranger to hosting big-name talent. Last year they had the Gin Blossoms, and in the past they’ve had bands like Everclear, the Spin Doctors, Rusted Root and the Smithereens.


This festival feels like everything you could want in a fall day. The event is lovingly planned by a group of 20 well-connected locals in support of the Pound Ridge Partnership, which is an independent, not-for-profit that seeks to make Pound Ridge a more inviting and inclusive place to live, work and play. This year marks their 10th festival. In that time, it’s grown from a few hundred people in attendance to upwards of seven thousand, but it’s kept its small-town feel, and the original committee that founded it.


It wouldn’t be an Octoberfest without libations, so the organizers make sure their beverage gardens include plenty of fall-flavored craft beer and carefully-selected wines. We also heard a rumor (from the co-chair) that they might have pink rosè cider again this year, so be on the lookout for that.


With an emphasis on fall flavors and local purveyors, the festival’s food is the perfect complement to the Octoberfest-inspiration behind the event. From cookout-style grabs off the grill, to fresh-from-the-oven pizza, to food truck offerings to satisfy any palette, to giant soft pretzels (of course!) and desserts to sweet talk your sweet tooth, the Harvest Fest’s offerings are enough to keep everyone full and happy.


Root beer garden? Yes, please! The kids’ area includes rides, bounce houses, face painting, carnival games, and crafts like pumpkin and cookie decorating. Kids will have their own food and beverage offerings too, including root beer floats, cotton candy and apple cider. Each activity or snack costs a certain amount of tickets, so be sure to buy some when you get there.

Cute story behind the Root Beer Garden: Many years ago, when Co-Chair Kevin Long’s son was little, Kevin took him on a tour of the festival grounds before the event. Kevin was pointing out where everything would go – i.e. ‘Here’s where the stage will go. Here’s where the beer garden will be. Here’s the kids’ area…’ Upon hearing that, his son asked if the kids’ area was where the Root Beer Garden would live. And ever since then, the kids’ Root Beer Garden has been a hallmark of the event.


Pound Ridge Town Park is a beautiful setting in one of the most picturesque towns in Westchester. The leaf peeping alone is worth the trip. Fun fact: back in the 1800s, the Pound Ridge Town Park hosted an annual farmer’s fair that gathered hundreds of farmers and patrons to the area. To Co-Founder Kevin Long, this feels like the chosen location brings the event back to Pound Ridge’s roots.


From the 20-person committee that organizes the event, to the array of activities designed to keep kids entertained, the Pound Ridge Harvest Festival seeks to create an event where everyone feels like family – welcome, taken care of, and ready to have a good time. As Co-Chair Kevin Long puts it, “The Harvest Festival is such a family-friendly event. In the early days of planning it, most of us had little kids, so we knew what would keep them entertained and what would let their parents to have a good time too. We’ve kept those things, as the festival’s grown, and we’ve added lots of amenities and special surprises each year. We keep striving to do better year after year. This is such a special festival, in such a special place.”


Free to enter

Parking + shuttle to Town Park: $25/car

VIP Tickets: $150 (sold out)


City Winery Hudson Valley

23 Factory St, Montgomery, NY 12549

Most people know the name “City Winery.” Some people are surprised to hear that the Hudson Valley has one of its own.

City Winery Hudson Valley opened its doors in June 2020. It is one of several locations throughout the country, the first being in Manhattan. Each City Winery follows the same ideals: keep the shows intimate and the experiences elevated. All locations under the City Winery name are owned and operated by Michael Dorr, who is known for his uncompromising standards when it comes to wine, food and music.

The historic Montgomery Worsted Mills is the chosen site for City Winery’s Hudson Valley location. The 22-acre property lies on the Wallkill River. It includes a fully operational winery, restaurant, tasting room, and a tribute band show venue for private events and shows. What makes this space especially unique is that it is the only operating winery in New York completely run by a hydro generator, which is powered by water from the Wallkill River, and stored in a manmade dam built behind the property that dates back to 1890.

City Winery has built a reputation for crafting intimate live music experiences for its audience. Its Hudson Valley location is no different. Though it sheds the urban setting of its New York predecessors, it takes full advantage of its ample, upstate property. The sprawling, industrial interior houses a restaurant, several event spaces and a stage. Outdoors, there’s an amphitheater on its vast lawn where it hosts “Concerts in the Vineyard” during the summer and early fall.

The amphitheater’s vintage stone stage overlooks the Wallkill River and is surrounded by the vineyards that bear much of the wine they serve. Yorktown mom of three, Sofia Robinson, recently attended one of the Concerts in the Vineyard. Remarking on the experience, she said, “My husband surprised me with a VIP tent at a Concert in the Vineyard in July. The food was delicious, the wine was plentiful, and the music was great. I’ve never been to a concert in a setting this beautiful. All my guests had a great time, and I’d go back in a heartbeat.”

In addition to their warm-weather outdoor concert offerings, throughout the year, City Winery Hudson Valley hosts concerts from all different genres of music in their indoor mainstage, and each week they host “Wine Down Wednesdays,” which feature music from local artists.


September 13 – Old 97s – The Falls Room

September 15 – Glenn Tilbrook – The Falls Room

September 25 –  JOHNNYSWIM – Concerts in the Vineyard

October 26 – Augustana – The Falls Room

Arrowood Farms

236 Lower Whitfield Rd, Accord, NY 12404

Arrowood Farms is an upstate escape that’s carving out a name for itself as a live music destination. Arrowood is also a farm brewery, distillery, restaurant and event space that values local sourcing for its beer, spirits and food. This fall, Arrowood Farms will host both the Woodsist Festival on September 24-25, and the Felice County Fair on October 1. Both are co-productions of Impact Concerts and Ground Control Touring.

As event producer Drew Frankel from Impact Concerts told us, “Arrowood is a truly magical place for live music nestled between the Catskill Mountains and the Shawangunks. The picturesque setting is complemented by fantastic local food and craft vendors, and of course, excellent beer and spirits made from local ingredients and brewed and distilled on-site.”

Woodsist Festival

Named after Woodsist Records, which is also a producer of the festival, the Woodsist Festival is filled to the gills with indie gold. Saturday’s lineup includes Guided by Voices, Bill Callahan, Woods, The Feelies, Pachyman, Myriam Gendron, The Red, Pinks & Purples, DJ Jocelyn Romo. The lineup for Sunday features Waxahatchee, Sun Ra Arkestra, Medeski Martin Duo, Mind Maintenance, Laraaji, Mary Lattimore, Bonny Doon, Tubby’s DJ’s.


2-Day Pass: $200

Saturday: $110

Sunday: $110

Kids under 10 free with a ticketed adult.

Tickets and More Info: 

Felice County Fair

After a couple years off, Felice County Fair is back! This unique, one-day festival is almost like a backyard jam session – but with big-name indie talent, a beautiful location, and a couple thousand friends.

The lineup includes “unique and collaborative sets” with performances by: Conor Oberst, the Felice Brothers, Hurray for the Riff Raff, Evan Stephens Hall (of Pinegrove), Haley Heynderickx, Al Olender, and William Lawrence.

Worth noting, members of the Felice Brothers plan to perform with each of the artists, to give festivalgoers a one-of-a-kind show. As James Felice describes it, “This festival basically is in our home, surrounded by our friends and family, and in doing it, we get to introduce the people we love to some of our favorite musicians. Our plan with Felice County Fair is to join most or all of the bands and artists on stage, creating a truly unique day of music that will not be repeated anywhere, ever again.”


GA: $80

VIP: $160

Kids under 10 free with a ticketed adult.

Tickets and More Info:

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About the Author: Liz Goodyear