New London County

New London, Groton, Mystic, Stonington, Waterford, Norwich, Lebanon and the communities of Southeastern Connecticut.

Middlesex County

Essex, Ivoryton, Old Saybrook, East Haddam, Haddam Neck, Durham, Portland and the lower Connecticut River Valley.

Washington County

Westerly, Charlestown, Narragansett, South Kingstown, Wickford and the Rhode Island shoreline.

Newport County

Newport, Middletown, Portsmouth, Jamestown, Tiverton and the coastal traditions of Aquidneck Island.

Connecticut Maritime Heritage Festival

Vessel tours, the Burning of Benedict Arnold, a military skills challenge and Eastern Connecticut's first drone light show over the Thames River.

Durham Fair

Connecticut's largest agricultural fair, now in its 106th year, with a midway, livestock, thousands of exhibits and main-stage music.

Wickford Harbor Fire

Floating fire pits on the harbor, live music around the village, food trucks and shops open late — free, and celebrating its tenth year.

Audrain Newport Concours & Motor Week

Four days of rare automobiles, seminars and gatherings, ending with the Concours d'Elegance at Fort Adams and a new Supercar Concours.

Harvest Fair at Norman Bird Sanctuary

A 52-year Aquidneck Island tradition: hayrides, the mud pit, artisan vendors, local food and music on 300 acres of sanctuary land.

U.S. Coast Guard Band at Avery Point

• Date: Monday, September 7, 2026 (Labor Day)
• Location: Branford House Lawn, UConn Avery Point, Groton, CT
• Admission: Free
• Best For: Picnics, families and the last summer sunset on the Sound

The full Coast Guard Band closes out the summer outdoors on the Branford House lawn. Bring chairs, a blanket and dinner, and let Labor Day end with a brass section and a water view.

Connecticut Maritime Heritage Festival

• Dates: Saturday and Sunday, September 12–13, 2026
• Venues: Fort Trumbull State Park and Waterfront Park, New London, CT
• Saturday Night: Burning of Benedict Arnold march on Bank Street at 7:30 p.m.; 300-drone light show over the Thames at about 8:30 p.m.
• Getting Around: Free water taxi and shuttle bus between venues
• Features: Military and private vessel tours, Coast Guard demonstrations, Sunday military skills challenge, kids' zone, live music

New London's signature maritime weekend adds something the region has never seen: a drone show over the river, visible from downtown. Park once, ride the water taxi between Fort Trumbull and the waterfront, and stay for the evening.

Groton City Brew Run

• Date: Saturday, September 12, 2026
• Time: 11:00 a.m. to 2:00 p.m.
• Area: City of Groton, CT
• After the Run: Brew festival, food trucks and community activities
• Benefit: Riverfront Children's Center

The Greater Mystic Chamber and Groton Utilities bring back the Brew Run — an active morning followed by local beer and food trucks, all for a good cause. Pair it with the Maritime Festival across the river for a full Saturday.

Mystic Garlic Festival

• Dates: Saturday and Sunday, September 19–20, 2026
• Location: Olde Mistick Village, 27 Coogan Boulevard, Mystic, CT
• Features: Garlic growers and farms, bakers, food vendors, crafters, artisans and live music
• Best For: Food lovers, families and an easy Mystic afternoon

Now in its 19th year, the Garlic Festival fills the village with growers, food vendors and makers. It is one of the few festivals where the shopping bag smells as good as the lunch.

Mystic Film Festival

• Dates: Thursday through Sunday, September 24–27, 2026
• Venues: Mystic Luxury Cinemas at Olde Mistick Village and venues in Westerly, RI
• Features: Independent features, shorts and documentaries, filmmaker Q&As and workshops
• Opening Night: Films by local filmmakers

The ninth annual festival brings independent film to both sides of the state line, with opening night devoted to work made right here. Tickets and passes are on sale now.

The Garde Turns 100

• Date: Saturday, October 3, 2026 at 6:00 p.m.
• Location: Garde Arts Center, 325 State Street, New London, CT
• The Evening: An immersive recreation of the theater's 1926 grand opening — newsreels, silent pictures, antique cars, a red carpet, klieg lights on State Street and a speakeasy lounge
• Also This Fall: Illusionist Leon Etienne (Sept. 26), Randy Travis (Oct. 1)

New London's movie palace celebrates its centennial by turning back the clock to opening night. Period costumes are encouraged, and Upper State Street becomes part of the show.

Connecticut Renaissance Faire

• Dates: Saturdays and Sundays through October 25, plus Labor Day and Columbus Day Mondays
• Hours: 10:30 a.m. to 6:00 p.m.
• Location: Lebanon Country Fairgrounds, 122 Mack Road, Lebanon, CT
• Admission: $18 general, $10 youth (7–15), children 6 and under free
• Themed Weekends: Dragons & Adventure (Labor Day), Roses & Romance, Shirefolk, Faerie Ring Revels, Pirate & Viking Invasion and more

Full-contact jousting, more than 200 artisan shops and a different theme every weekend across nine weekends. Free Kids Day on September 5 admits youth 7–15 free with a paid adult.

Haddam Neck Fair

• Dates: Friday, September 4 through Monday, September 7, 2026
• Admission: General admission listed at $15; kids under 12 free
• Parking: Free
• Best For: Families, livestock, rides, food and Labor Day tradition

The Connecticut River Valley's Labor Day fair opens this issue's fair season: agricultural exhibits, animals, entertainment, midway rides and the unmistakable atmosphere of a classic country fair.

Connecticut Audubon Tree Swallow Cruises

• Remaining Dates: September 5, 13 and 20
• Departure Windows: Approximately 3:30–5:00 p.m., depending on date
• Length: Approximately 3.5 hours
• Departure: Essex Steam Train & Riverboat area, Essex, CT
• Best For: Nature, photography, birds and river sunsets

Three chances remain to watch hundreds of thousands of tree swallows gather over the lower Connecticut River at sunset before funneling into their roost — one of the great seasonal spectacles in New England.

September at The Kate

• September 4: Reverend Horton Heat, 8:00 p.m.
• September 5: D.A. Foster & the Shaboo All Stars, 8:00 p.m.
• September 13: Mike DelGuidice of Billy Joel's band, 7:00 p.m.
• September 19: The Linda Ronstadt Experience, 3:00 p.m.
• September 25: 40 Fingers, 8:00 p.m.
• Location: The Kate, 300 Main Street, Old Saybrook, CT

Old Saybrook's 284-seat theater keeps a full September calendar, from rockabilly to a night with Billy Joel's longtime touring vocalist. Arrive early and visit the Katharine Hepburn Museum off the lobby.

The Snow Goose — World Premiere

• Run: Now playing through October 18, 2026
• Location: The Goodspeed, 6 Main Street, East Haddam, CT
• Based On: Paul Gallico's novel
• Best For: Theatre, new works and Connecticut River weekends

Goodspeed's world-premiere musical settles into its run this month. A brand-new production in one of Connecticut's most historic theaters is a strong anchor for a fall day in East Haddam.

Durham Fair

• Dates: Thursday, September 24 through Sunday, September 27, 2026
• Hours: Thursday 4–10 p.m.; Friday and Saturday 9 a.m.–10 p.m.; Sunday 9 a.m.–6 p.m.
• Admission: Thursday $10 for all; Friday–Sunday $20 adults, $10 seniors, children 11 and under free
• Location: Durham Fairgrounds, Routes 17 & 68, Durham, CT
• Features: Midway, livestock competitions, thousands of exhibits and national country acts on the main stage at no extra charge

The 106th Durham Fair is the largest agricultural fair in Connecticut and a full weekend in itself. Discounted advance tickets are sold online through midnight on September 24.

Ivoryton Playhouse: Closing One, Opening Another

• Come From Away: Final performances through Sunday, September 6
• The AfterParty: Annual fundraiser, Saturday, September 19 from 5:00 p.m.
• A Piece of My Heart: October 1–25, the true stories of six women who served in Vietnam
• Location: Ivoryton Playhouse, 103 Main Street, Ivoryton, CT

The Playhouse's America 250 season turns a corner this month: the last week of Come From Away, a September fundraiser, and an October opening that honors the 250th anniversary of the Army, Navy and Marine Corps.

Portland Agricultural Fair

• Dates: Friday, October 2 (gates at 3 p.m.) through Sunday, October 4, 2026
• Location: 1401 Main Street, Portland, CT
• Features: Livestock shows, truck and tractor pulls on one of New England's longest pull tracks, petting zoo, pony rides, aerobatic acts, rides and an entertainment tent
• Best For: Families and the last major fair of the Connecticut season

Portland closes the state's fair calendar with a bigger home and a Sunday mud bog. If you missed Durham, this is the encore.

Rhythm & Roots Festival

• Dates: Friday, September 4 through Sunday, September 6, 2026
• Location: Ninigret Park, Charlestown, RI
• Friday: Festival begins at noon; music begins at 1:00 p.m.
• Features: Cajun, zydeco, blues, bluegrass and Americana on three stages, dancing, food and camping

South County's big Labor Day sendoff. Ninigret Park becomes a three-day music community, and the dance tent is where the weekend actually happens.

General Stanton Jazz Fest

• Date: Sunday, September 13, 2026
• Time: 2:00 to 7:00 p.m.
• Location: General Stanton Inn, 4115 Old Post Road, Charlestown, RI
• Lineup: Dan Moretti & The Hammond Boys, Evening Sky, Joe & Paula Trio
• Tip: Bring a lawn chair

The second annual Jazz Fest follows August's blues festival on the same historic grounds — an easy Sunday afternoon of live jazz, food and lawn chairs.

Surftown Half Marathon, Relay & 5K

• Date: Sunday, September 13, 2026
• Half Marathon Start: 7:30 a.m.
• 5K Start: 7:40 a.m.
• Start/Finish Area: Misquamicut / Wuskenau Town Beach area
• Course: Watch Hill, Weekapaug and the Westerly coastline

One of southern New England's most scenic road races runs the length of the Westerly shoreline before finishing back at the beach.

Wickford Harbor Fire — 10th Anniversary Season

• Date: Friday, September 18, 2026 (final fire of the season October 16)
• Time: 5:30 to 9:00 p.m.
• Location: Brown and Main Streets, Wickford Village, North Kingstown, RI
• Admission: Free
• Features: Floating fire pits on the harbor, live music around the village, food trucks, free face painting and petting zoo, shops open late

Ten years in, Harbor Fire has become one of the shoreline's best free nights out. Stroll the village, follow the music from block to block, and watch the fires glow on the water.

Fayerweather Fall Festival & Outdoor Craft Market

• Date: Saturday, September 19, 2026
• Location: Fayerweather Craft Guild, 1895 Mooresfield Road, Kingston, South Kingstown, RI
• Apple Crisp: With ice cream and a beverage for $5, 11:00 a.m. to 2:00 p.m.
• Best For: Local craft vendors, a small-town Saturday and the first apple crisp of the season

A modest, well-loved South Kingstown tradition on the grounds of the historic Fayerweather House — the kind of event that marks the season more than any calendar does.

General Stanton Sunday Market

• Schedule: Sundays through September 20, 2026
• Location: General Stanton Inn, Charlestown, RI
• Best For: Local makers, small businesses and a slow Sunday

Three Sundays remain in the season for the market at the General Stanton Inn. Browse locally, then stay for lunch.

Newport International Polo: The Final Month

• September 5: USA vs. England
• September 12: American Polo Classic
• September 19: USA vs. Switzerland
• September 26: Season Finals
• Start Time: 4:00 p.m. in September
• Location: Newport Polo Grounds, 250 Linden Lane, Portsmouth, RI

The 150th-anniversary season closes with four Saturdays of international matches, tailgating and divot stomping. Schedules can shift, so confirm the match before you pack the picnic.

IYRS Newport Classic Yacht Regatta

• Dates: Saturday and Sunday, September 5–6, 2026
• Host: IYRS School of Technology & Trades, Thames Street, Newport, RI
• Features: Ocean racing, a parade of classic boats and an awards ceremony
• Best For: Wooden-boat lovers and anyone with a spot on the harbor

The 47th edition of Newport's classic-yacht weekend fills the harbor with varnish and canvas. Watch the parade from the waterfront and the racing from Fort Adams.

Newport International Boat Show

• Dates: Thursday, September 17 through Sunday, September 20, 2026
• Hours: 10 a.m.–6 p.m. Thursday through Saturday; 10 a.m.–5 p.m. Sunday
• Location: Newport Yachting Center and the downtown waterfront
• Parking Tip: Easton's Beach with a shuttle, or the Jamestown–Newport ferry with free Jamestown parking

Seventeen acres of boats, gear and seminars turn the harbor into one of New England's largest marine marketplaces. It runs rain or shine.

12 Metre North American Championship

• Dates: Friday through Sunday, September 18–20, 2026
• Where to Watch: Fort Adams, Castle Hill, Bannister's Wharf and Goat Island
• Cost: Free from shore
• Best For: Sailing history, photography and a reason to walk the harbor during Boat Show weekend

The historic 12 Metre yachts of America's Cup legacy race in Traditional and Classic divisions on the bay. Castle Hill offers the elevated view; Fort Adams puts you closest to the marks.

Newport Mansions Wine & Food Festival

• Dates: Friday, September 18 through Sunday, September 20, 2026
• Primary Location: Rosecliff, 548 Bellevue Avenue, Newport, RI
• Features: Tastings, expert-led seminars, a celebration of local chefs and a Sunday jazz brunch
• Best For: Food, wine and a Gilded Age weekend

The 21st annual festival brings chefs, winemakers and spirits to Bellevue Avenue's most theatrical setting. It shares the weekend with the Boat Show and the 12 Metre racing — book lodging early.

Cider Fest at Newport Vineyards

• Date: Sunday, September 20, 2026
• Time: 12:00 to 5:00 p.m.
• Location: Newport Vineyards, 909 East Main Road, Middletown, RI
• Features: House-made ciders, seasonal food, live music and family activities

More than 30 years running, Cider Fest is the island's low-key answer to Wine & Food weekend: in-house ciders, music on the lawn and something for the kids to do.

Audrain Newport Concours & Motor Week

• Dates: Thursday, October 1 through Sunday, October 4, 2026
• Concours d'Elegance: Sunday, October 4, 8:30 a.m.–4:00 p.m. at Fort Adams State Park
• New in 2026: A Supercar & Hypercar Concours on Saturday, October 3, and a 50-mile Supercar Drive on Thursday
• Also: The Gathering at Rough Point, seminars with Jay Leno, the Concours Village at the International Tennis Hall of Fame
• Getting There: Complimentary trolley loops and ferry service to Fort Adams from Jamestown and Newport

Named Motoring Event of the Year at the International Historic Motoring Awards, the seventh Motor Week adds a second concours for the first time. Ticketing varies by event.

52nd Annual Harvest Fair

• Dates: Saturday and Sunday, October 3–4, 2026
• Location: Norman Bird Sanctuary, 583 Third Beach Road, Middletown, RI
• Admission: $14 general; $10 ages 3–18; free under 3
• Early Bird: Discounted tickets with expedited entry through September 15
• Features: Hayrides, the mud pit, Mabel's barrel train, midway games, more than 40 food and craft vendors, live music

Since 1974, the Harvest Fair has defined the season on Aquidneck Island. More than 10,000 people come through in a weekend; the early-bird tickets are worth grabbing before mid-September.

Beavertail Lighthouse Tower Climb Days

• Season: Select dates between September 7 and October 12, 2026
• Hours: 1:30 to 4:00 p.m.
• Location: Beavertail Lighthouse Museum, Beavertail Road, Jamestown, RI
• Best For: Families, photographers and a windy view of Narragansett Bay's mouth

The tower opens for climbs on select afternoons this fall. Check the museum's schedule for exact dates, then stay for the tide pools and the sunset at Beavertail State Park.