Festivals near Middletown, CT.

Sarah Brightman: A Winter Symphony

• Nov. 29 - Nov 29, 2025
• Mohegan Sun Arena - Montville, CT USA

• $50 - $100

Every year she shares her critically acclaimed holiday show with audiences in countries around the world… and this year is no exception! Sarah is exci ....

Allman Brothers Tribute @ FTC Stage One

• Nov. 29 - Nov 29, 2025
• StageOne at FTC - Fairfield, CT USA

• $25 - $50

This powerhouse tribute to the Allman Brothers Band has been earning rave reviews from fans and venues alike. Their performances capture the spirit, e ....

2025 Fireside Oyster Hour at Weekapaug Inn

• Nov. 21 - Nov 21, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

Ann's Place 23rd Annual Festival of Trees

• Nov. 21 - Nov 23, 2025
• The Summit at Danbury - Danbury, CT USA

• $1 - $10

Danbury, CT – Ann’s Place proudly presents the 23rd Annual Festival of Trees: “Honoring Hope” from November 21–23, 2025 at The Summit at Danbury. Hono ....

Ann's Place Festival of Trees

• Nov. 21 - Nov 23, 2025
• The Summit at Danbury - Danbury, CT USA

• $1 - $10
• $10 - $25
• $50 - $100

Ann’s Place proudly announces its 23rd Annual Festival of Trees: Honoring Hope. Celebrating courage, resilience, and community, Ann’s Place brings sup ....

Ten-Play Play Festival

• Nov. 19 - Nov 19, 2025
• MoCA CT - Westport, CT USA

• $10 - $25

A Chronicles Presents: Winners of its Annual 10-Minute Play Festival Visionary, Absurd, Heartbreaking. Nine Playwrights on Reproductive Rights Novemb ....

2025 Fireside Oyster Hour at Weekapaug Inn

• Nov. 14 - Nov 14, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

Barrels For A Cause 2025

• Nov. 13 - Nov 13, 2025
• Stappa Vineyard - Orange, CT USA

• Food / Wine / Beer

• $100 - $250

Join the Rape Crisis Center of Milford & the Beth-El Center on Thursday November 13th for our 3rd annual Barrels for a Cause event at Stappa Vineyard! ....

2025 Fireside Oyster Hour at Weekapaug Inn

• Nov. 7 - Nov 7, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

2025 Fireside Oyster Hour at Weekapaug Inn

• Oct. 31 - Oct 31, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

Hartford Skelly Run

• Oct. 25 - Oct 25, 2025
• Hartford - Hartford, CT USA

• Holiday (Halloween)
• Holiday (Other)
• Outdoor / Recreation
• Seasonal (Fall)
• Sports / Fitness

• $50 - $100
• $100 - $250

Get ready to lace up your running shoes for the most spine-tingling fun run of the year "Skelly Run"!Inspired by the beloved 12ft Halloween decoration ....

2025 Fireside Oyster Hour at Weekapaug Inn

• Oct. 24 - Oct 24, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

Connecticut Food Truck & Wine Festival

• Oct. 19 - Oct 19, 2025
• Priam Vineyards a Winiarski Family Vineyard - Colchester, CT USA

Welcome to the Connecticut Food & Wine Festival taking place on the beautiful grounds of Priam Vineyards October 18 & 19 from 11-6. This Free admissio ....

Connecticut Food Truck & Wine Festival

• Oct. 18 - Oct 18, 2025
• Priam Vineyards a Winiarski Family Vineyard - Colchester, CT USA

Welcome to the Connecticut Food & Wine Festival taking place on the beautiful grounds of Priam Vineyards October 18 & 19 from 11-6. This Free admissio ....

Fireside Oyster Hour at Weekapaug Inn

• Oct. 17 - Oct 17, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

2025 Fireside Oyster Hour at Weekapaug Inn

• Oct. 17 - Oct 17, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

Eversource Hartford Marathon and Half Marathon, Charity 5K and Team 26.2 Relay

• Oct. 11 - Oct 11, 2025
• Bushnell Park - Hartford, CT USA

• Sports / Fitness

• $10 - $25

Be inspired in Hartford with a glorious start in front of the majestic Capitol. Marathon and half marathon courses venture into the welcoming neighbor ....

Fireside Oyster Hour at Weekapaug Inn

• Oct. 10 - Oct 10, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

2025 Fireside Oyster Hour at Weekapaug Inn

• Oct. 10 - Oct 10, 2025
• Weekapaug Inn - Westerly, RI USA

• Food / Wine / Beer

• $50 - $100

Sit by the fireplace & enjoy two delicious varieties of oysters, which will be served on the half shell and paired with champagne and a selection of w ....

Vibe Cartel at Westport VFW

• Oct. 4 - Oct 4, 2025
• Veterans of Foreign Wars - Westport, CT USA

• Music

• $10 - $25

Get ready for an unforgettable night of groove and energy as Vibe Cartel takes the stage with their signature blend of fusion, funk, jazz, and rock. K ....

5th Annual Woodbridge Like Me Day

• Oct. 4 - Oct 4, 2025
• Woodbridge Town Green - Woodbridge, CT USA

Join us for the 5th Annual Woodbridge Like Me Day! Join us on Saturday, October 4 from 11 AM to 2 PM on the Woodbridge Town Green (Rain location: Am ....

South Windsor Apple Fest

• Oct. 4 - Oct 4, 2025
• 75 Brookfield St - South Windsor, CT USA

Enjoy 100+ vendors and international food trucks, signature apple pie and ice cream, apple donuts, wings, adult beverages, live music including the Sa ....

South Windsor Apple Fest

• Oct. 4 - Oct 4, 2025
• 75 Brookfield St - South Windsor, CT USA

• Arts (Arts & Crafts)
• Food / Wine / Beer
• Seasonal (Fall)

• FREE!!

More than 100 crafters, international food trucks, signature apple pie and ice cream, apple donuts, wings, adult beverages, live music with New Englan ....

Harvest Bounty German Fest

• Oct. 3 - Oct 3, 2025
• Litchfield Community Center - Litchfield, CT USA

• $1 - $10

Menu: German Food & Beer Band: Keith's Polkaparty Band * Pre-registration REQUIRED BY Wednesday Oct. 1st ....

Brew Moments with Cafely This National Coffee Day

• Sep. 29 - Sep 29, 2025
• Cafely - Norwich, CT USA

• Food / Wine / Beer

• FREE!!

Hey there, coffee lover! Let’s raise a mug to National Coffee Day on September 29, a day to celebrate the rich, aromatic brew that fuels our mornings, ....