Toy Drive - Houzpital Property Damage

411 John Downey Drive New Britain, CT, 06051

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Ahavah: The Story of Christmas in Middletown

Ahavah: The Story of Christmas is celebrating TWENTY YEARS! Taking you back in time to experience the astonishing true story behind Christmas, Ahavah is a delight for the whole family. The joy and enchantment of the season are palpable in this telling of a timeless s......More

Ahavah: The Story of Christmas is celebrating TWENTY YEARS! Taking you back in time to experience the astonishing true story behind Christmas, Ahavah is a delight for the whole family. The joy and enchantment of the season are palpable in this telling of a timeless story. Ekklesia Contemporary Ballet and Ekklesia School of Ballet join together once more to present Ahavah!

Middletown High School 200 La Rosa Lane Middletown, CT

Live Music at Seaview Bistro at Water's Edge Resort & Spa

Enjoy Live Music every Friday & Saturday At Seaview Bistro At the Water's Edge Resort & Spa From 9:00 p.m. to Midnight.   Questions:  Contact Email - [email protected] 

Water's Edge Resort & Spa At Seaview Bistro 1525 Boston Post Road Westbrook, CT 06498

HK Craft Fair

The 37th Annual HK Holiday Craft Fair returns with 80 local artists and crafters. Enjoy food trucks, a raffle with prizes donated by our crafters, a book fair, and kids’ activities. Free Admission! You’ll find the perfect gift right here. Discover something beautiful wh......More

The 37th Annual HK Holiday Craft Fair returns with 80 local artists and crafters. Enjoy food trucks, a raffle with prizes donated by our crafters, a book fair, and kids’ activities. Free Admission! You’ll find the perfect gift right here. Discover something beautiful while supporting local small businesses. Visit our website for more information https://hkyfs.org/hk-craft-fair/

Haddam-Killingworth Middle School

Holiday on Main Street presents Magic of Middletown

10:00 AM to 2:00 PM Please visit www.holidayonmain.com for all Holiday on Main Street dates and events!

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Holiday Jamboree Tea at the Westbrook Inn Bed and Breakfast

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not i......More

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not issue refunds or credits. Click here to purchase your tickets. 

Westbrook Inn Bed and Breakfast 976 Boston Post Road Westbrook, CT 06498

Ahavah: The Story of Christmas in Middletown

Ahavah: The Story of Christmas is celebrating TWENTY YEARS! Taking you back in time to experience the astonishing true story behind Christmas, Ahavah is a delight for the whole family. The joy and enchantment of the season are palpable in this telling of a timeless s......More

Ahavah: The Story of Christmas is celebrating TWENTY YEARS! Taking you back in time to experience the astonishing true story behind Christmas, Ahavah is a delight for the whole family. The joy and enchantment of the season are palpable in this telling of a timeless story. Ekklesia Contemporary Ballet and Ekklesia School of Ballet join together once more to present Ahavah!

Middletown High School 200 La Rosa Lane Middletown, CT

Ahavah: The Story of Christmas in Middletown

Ahavah: The Story of Christmas is celebrating TWENTY YEARS! Taking you back in time to experience the astonishing true story behind Christmas, Ahavah is a delight for the whole family. The joy and enchantment of the season are palpable in this telling of a timeless s......More

Ahavah: The Story of Christmas is celebrating TWENTY YEARS! Taking you back in time to experience the astonishing true story behind Christmas, Ahavah is a delight for the whole family. The joy and enchantment of the season are palpable in this telling of a timeless story. Ekklesia Contemporary Ballet and Ekklesia School of Ballet join together once more to present Ahavah!

Middletown High School 200 La Rosa Lane Middletown CT

A Tribute to Frank Sinatra & Dino at Water's Edge Resort & Spa

Frank Sinatra was known as “The Chairman of the Board” and remains an Icon of Music, Television, & Film to this day. Dean Martin was nicknamed “The King of Cool” and doesn’t that just say it all! Enjoy an evening with Sounds of Sinatra and Dino as they bring the mus......More

Frank Sinatra was known as “The Chairman of the Board” and remains an Icon of Music, Television, & Film to this day. Dean Martin was nicknamed “The King of Cool” and doesn’t that just say it all! Enjoy an evening with Sounds of Sinatra and Dino as they bring the music of these Two Icons to the Connecticut Shoreline. Guests purchasing fewer than 10 tickets will be seated at tables with other guests. For more Information and to make Reservations, CLICK HERE  

Water's Edge Resort & Spa 1525 Boston Post Road Westbrook, CT

Live Music at Seaview Bistro at Water's Edge Resort & Spa

Enjoy Live Music every Friday & Saturday At Seaview Bistro At the Water's Edge Resort & Spa From 9:00 p.m. to Midnight.   Questions:  Contact Email - [email protected] 

Water's Edge Resort & Spa At Seaview Bistro 1525 Boston Post Road Westbrook, CT 06498

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Power in Conversation "A Fireside Chat with Inspiring Women" presented by WLC

Terrazza Restaurant, Quarry Ridge Golf Course, 9 Rose Hill Rd, Portland, CT 06480

Trivia with Dave Lefkin in the Choo Choo Lounge at Saybrook Point

Get ready for a fun-filled evening of trivia every Monday night with Dave Lefkin at the Choo Choo Lounge! Test your knowledge, challenge your friends, starting at 7 PM. Enjoy a delicious dinner from our menu and sip on your favorite drinks from the full bar......More

Get ready for a fun-filled evening of trivia every Monday night with Dave Lefkin at the Choo Choo Lounge! Test your knowledge, challenge your friends, starting at 7 PM. Enjoy a delicious dinner from our menu and sip on your favorite drinks from the full bar while you play. It’s the perfect way to kick off your week with fun, food, and friendly competition. See you there!

Saybrook Point Resort and Marina The Choo Choo Lounge 2 Bridge Street Old Saybrook, CT. 06745

Chamber Connects

Are you looking to connect with fellow chamber members for lead generation and relationship building?! Look no further than the chamber's new bi-weekly networking group, "Chamber Connects"! Join us as you create meaningful opportunities by actively supporting fellow......More

Are you looking to connect with fellow chamber members for lead generation and relationship building?! Look no further than the chamber's new bi-weekly networking group, "Chamber Connects"! Join us as you create meaningful opportunities by actively supporting fellow members. Share referrals, recommend services, and open doors—not just to fill a business pipeline, but to grow your influence, confidence, and visibility within a trusted network. Participate in our introductory event which will feature introductions, a review of the Chamber Connects program, and much more!

Courtyard by Marriott Hartford Cromwell 4 Sebethe Dr Cromwell, CT 06416

Economic Development Consortium Steering Committee

The Economic Development Consortium operates with a goal of promoting and supporting a robust and appropriate economic environment in the Middlesex Chamber footprint and in so doing, grow and retain jobs, businesses, and capital investment within our region. This gro......More

The Economic Development Consortium operates with a goal of promoting and supporting a robust and appropriate economic environment in the Middlesex Chamber footprint and in so doing, grow and retain jobs, businesses, and capital investment within our region. This group, made up of local Economic Development Directors and representatives from each town meet on a monthly basis to share ideas, collaborate, and support one another through various projects that affect our region.  

City of Middletown 245 Dekoven Drive Middletown, CT

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Fireside Holiday Tea at The Westbrook Inn

Cozy up by the fire with our festive Holiday Afternoon Tea — a charming seasonal escape featuring delicate sandwiches, sweet treats, and soothing teas in the warm glow of The Westbrook Inn's inviting hearth. Indulge in a two-hour tea service featuring a choice of two......More

Cozy up by the fire with our festive Holiday Afternoon Tea — a charming seasonal escape featuring delicate sandwiches, sweet treats, and soothing teas in the warm glow of The Westbrook Inn's inviting hearth. Indulge in a two-hour tea service featuring a choice of two gourmet teas, delicate finger sandwiches, cookies, a warm scone with jam and crème fraîche, and more!  Tickets are $49.95 per person + tax. Gratuity Not Included. We are sorry but we do not issue refunds or credits.

Westbrook Inn Bed & Breakfast 976 Boston Post Road Westbrook, CT 06498

Credit Basics and Beyond

Gain a clear and practical understanding of how credit works! Learn what credit scores are, how they’re calculated, and why they matter. Explore how to read a credit report, build and maintain good credit, manage debt wisely, and avoid common financial mistakes. ......More

Gain a clear and practical understanding of how credit works! Learn what credit scores are, how they’re calculated, and why they matter. Explore how to read a credit report, build and maintain good credit, manage debt wisely, and avoid common financial mistakes. Perfect for anyone looking to strengthen their financial knowledge and make confident credit decisions. Register today!

Chelsea Groton Bank Sprague Branch 156 Willimantic Road Sprague, CT

LIve Music in the Choo Choo Lounge at Saybrook Point

Enjoy live music every Tuesday, Wednesday, and Thursday at Saybrook Point! Featuring a variety of talented local artists, each night brings a unique musical experience. Relax, unwind, and enjoy a delicious dinner from our menu and drinks from the bar while ......More

Enjoy live music every Tuesday, Wednesday, and Thursday at Saybrook Point! Featuring a variety of talented local artists, each night brings a unique musical experience. Relax, unwind, and enjoy a delicious dinner from our menu and drinks from the bar while you soak in the tunes.

Saybrook Point Resort and Marina The Choo Choo Lounge 2 Bridge Street Old Saybrook, CT. 06475

Durham/Middlefield Division

The Chamber has nine geographically based divisions which meet on a monthly basis throughout Middlesex County. These divisions focus on local economic development issues and each meeting features an update from local municipal officials.  Meetings occur on the second......More

The Chamber has nine geographically based divisions which meet on a monthly basis throughout Middlesex County. These divisions focus on local economic development issues and each meeting features an update from local municipal officials.  Meetings occur on the second Wednesday of the month at different locations. This division does not meet in the Summer months of July and August. The host for this meeting is TSG located at 422 Main Street, Durham, CT. Torrison Stone & Garden offers complete outdoor solutions through their integrated Stone, Garden, and Design services. They understand that when homeowners begin thinking about upgrading their outdoor spaces, the process can feel overwhelming. That’s why their team works closely with each client to clarify the scope of the project—starting with how the space will be used and what fits within the budget. The Chamber would like to thank the entire team at TSG for hosting our meeting. Agenda   I. Welcome and Introductions Introductions from the division chair/s Round Robin introduction from members attending  II. Remarks Host remarks and information Town updates from department heads attending Speaker remarks and information III. Closing Remarks and Chamber Updates Chamber updates from Chamber representative attending

TSG (Torrison Stone & Garden) 422 Main Street Durham, CT

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Ask a Lender: Homebuying & Credit Drop-In Event

Have questions about buying a home or improving your credit? Stop by anytime between 11 AM and 3 PM or schedule a one-on-one chat with a Chelsea Groton Bank lender. Whether you're just exploring your options or ready to take the next step, we're here to help, with......More

Have questions about buying a home or improving your credit? Stop by anytime between 11 AM and 3 PM or schedule a one-on-one chat with a Chelsea Groton Bank lender. Whether you're just exploring your options or ready to take the next step, we're here to help, with no obligation to get a loan. Come on your lunch break! We'll have food available while you get your questions answered in a relaxed, friendly setting. Walk-ins welcome. Appointments encouraged. Let’s talk about your financial future, on your terms.

Hartford Public Library Albany Branch 1250 Albany Avenue Hartford, CT 06112

Holiday Jamboree Tea at the Westbrook Inn Bed and Breakfast

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not i......More

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not issue refunds or credits. Click here to purchase your tickets. 

Westbrook Inn Bed and Breakfast 976 Boston Post Road Westbrook, CT 06498

LIve Music in the Choo Choo Lounge at Saybrook Point

Enjoy live music every Tuesday, Wednesday, and Thursday at Saybrook Point! Featuring a variety of talented local artists, each night brings a unique musical experience. Relax, unwind, and enjoy a delicious dinner from our menu and drinks from the bar while ......More

Enjoy live music every Tuesday, Wednesday, and Thursday at Saybrook Point! Featuring a variety of talented local artists, each night brings a unique musical experience. Relax, unwind, and enjoy a delicious dinner from our menu and drinks from the bar while you soak in the tunes.

Saybrook Point Resort and Marina The Choo Choo Lounge 2 Bridge Street Old Saybrook, CT. 06475

Side Street to Main Street Business & Leadership Development Program Class 25 Session 9

The Side Street to Main Street Business & Leadership Development  Program, a one year long entrepreneurial and business development course, with a rigorous curriculum, was specifically designed to assist minority small business owners in the community, who did not have ......More

The Side Street to Main Street Business & Leadership Development  Program, a one year long entrepreneurial and business development course, with a rigorous curriculum, was specifically designed to assist minority small business owners in the community, who did not have formal business training, to become more successful by developing the attitudes, skills and qualities necessary for effective business ownership and success, taking them from the Side Street to the Main Street of the business community.   For more detailed information on Minority Entrepreneurial and Business Programs, Email: [email protected] or visit: https://www.middlesexchamber.com/side-street-to-main-street-program/

Middletown Police Department Community Room 222 Main Street Middletown, CT

Cromwell Division

The Chamber has nine geographically based divisions which meet on a monthly basis throughout Middlesex County. These divisions focus on local economic development issues and each meeting features an update from local municipal officials. In November, March and August......More

The Chamber has nine geographically based divisions which meet on a monthly basis throughout Middlesex County. These divisions focus on local economic development issues and each meeting features an update from local municipal officials. In November, March and August, our monthly morning division meetings are held during the evening and feature appetizers and networking, with the goal of creating new connections. The Cromwell Division occurs on the second Thursday of the month at different locations. This division does not meet in the month of July. CARA SCIANNA, CHAIRWOMAN Invites you to  THE CROMWELL DIVISION MEETING THURSDAY, DECEMBER 11, 2025  AT MATTABASSETT DISTRICT 245 Main Street 7:30 a.m. — 9:00 a.m.    Town updates will be given by the following Departments Mayor Town Manager Planning Office Police Dept. Fire Dept. Public Works Dept. Town Clerk’s Office Recreation Dept. Board of Education Mattabassett District Update Cromwell Children’s Coalition Update Cromwell Creative District Update Middlesex Chamber Update on upcoming meetings & events A complimentary continental breakfast will be available, courtesy of Mattabassett District from 7:30 – 8:00 a.m. & Networking with Members!  Meeting begins promptly at 8:00 a.m. and ends by 9:00 a.m.  

Mattabassett District 245 Main Street Cromwell, CT

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Holiday Jamboree Tea at the Westbrook Inn Bed and Breakfast

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not i......More

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not issue refunds or credits. Click here to purchase your tickets. 

Westbrook Inn Bed and Breakfast 976 Boston Post Road Westbrook, CT 06498

Fireside Holiday Tea at The Westbrook Inn

Cozy up by the fire with our festive Holiday Afternoon Tea — a charming seasonal escape featuring delicate sandwiches, sweet treats, and soothing teas in the warm glow of The Westbrook Inn's inviting hearth. Indulge in a two-hour tea service featuring a choice of two......More

Cozy up by the fire with our festive Holiday Afternoon Tea — a charming seasonal escape featuring delicate sandwiches, sweet treats, and soothing teas in the warm glow of The Westbrook Inn's inviting hearth. Indulge in a two-hour tea service featuring a choice of two gourmet teas, delicate finger sandwiches, cookies, a warm scone with jam and crème fraîche, and more!  Tickets are $49.95 per person + tax. Gratuity Not Included. We are sorry but we do not issue refunds or credits.

Westbrook Inn Bed & Breakfast 976 Boston Post Road Westbrook, CT 06498

LIve Music in the Choo Choo Lounge at Saybrook Point

Enjoy live music every Tuesday, Wednesday, and Thursday at Saybrook Point! Featuring a variety of talented local artists, each night brings a unique musical experience. Relax, unwind, and enjoy a delicious dinner from our menu and drinks from the bar while ......More

Enjoy live music every Tuesday, Wednesday, and Thursday at Saybrook Point! Featuring a variety of talented local artists, each night brings a unique musical experience. Relax, unwind, and enjoy a delicious dinner from our menu and drinks from the bar while you soak in the tunes.

Saybrook Point Resort and Marina The Choo Choo Lounge 2 Bridge Street Old Saybrook, CT. 06475

Combined Chester/Deep River/Essex & Westbrook Division

The Chester / Deep River / Essex and Westbrook Divisions will be joining forces for a combined meeting this December. Join us for a terrific networking opportunity and meet your fellow members from across the region.  There will be a "Corniest Holiday Joke" contest ......More

The Chester / Deep River / Essex and Westbrook Divisions will be joining forces for a combined meeting this December. Join us for a terrific networking opportunity and meet your fellow members from across the region.  There will be a "Corniest Holiday Joke" contest with prizes - bring the silliest, most eye-rolling dad-jokes to share and you could win!  The meeting will be hosted by The Connecticut River Museum.   Friday, December 12, 2025 8:00 to 9:00 a.m. Connecticut River Museum 67 Main Street, Essex

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Dashing Through Downtown Holiday Vehicle Parade 2025

Annual Decorated Vehicle Parade Friday, December 12, 2025 | Parade kicks off at 7:00 p.m. Join us for Middletown’s Annual Decorated Vehicle Parade! Decorate your car, van, truck, flatbed, company vehicle (a great free way to advertise your business!), sleigh—whatev......More

Annual Decorated Vehicle Parade Friday, December 12, 2025 | Parade kicks off at 7:00 p.m. Join us for Middletown’s Annual Decorated Vehicle Parade! Decorate your car, van, truck, flatbed, company vehicle (a great free way to advertise your business!), sleigh—whatever you’ve got. The more decorations, the better! Parade Details Registration: 4:30–6:30 p.m. at Middletown High School, 200 LaRosa Lane, Middletown Judging: 6:45 p.m. Parade Start: 7:00 p.m. sharp (don’t be late!) Route: Parade will travel from Middletown High School through Downtown Middletown, led by Santa himself! Participants will line up at Middletown High School before the parade begins. Santa and Mayor Gene Nocera will judge the Most Festive Vehicles—so bring your holiday spirit and creativity! We are asking for a $5 donation to help raise funds for Holiday on Main Street. Please also consider bringing an unwrapped toy to benefit the Middletown Police Department’s Toy Drive. Not participating but want to watch? Set up along Main Street, Middletown to catch all the decorated vehicles as they roll by and enjoy the holiday magic!

Parade Registration/Staging Area: Middletown High School 200 LaRosa Lane, Middletown

2025 Hoilday on Main Street Magic of Middletown Pub Crawl!

ELF-ed Up Pub Crawl Friday, December 12, 2025 - Downtown Middletown Join us for a festive night of holiday fun as we kick off the season with the ELF-ed Up Pub Crawl! Grab your friends, wear your best ugly holiday sweater, and get ready for an unforgettable evening ......More

ELF-ed Up Pub Crawl Friday, December 12, 2025 - Downtown Middletown Join us for a festive night of holiday fun as we kick off the season with the ELF-ed Up Pub Crawl! Grab your friends, wear your best ugly holiday sweater, and get ready for an unforgettable evening on Main Street. Event Highlights Ride on our decorated holiday pub-crawl bus which kicks off the night by participating in the Middletown Decorated Holiday Vehicle Parade Visit several Downtown Middletown establishments Take part in our Ugly Sweater Contest Enjoy giveaways, contests, laughs, and plenty of holiday cheer Schedule Snapshot A detailed schedule will be sent to all participants before the event, but here's a quick overview: 5:30 p.m. to 6:15 p.m. - Arrival & check-in 6:20 p.m. - Bus departs Downtown Middletown to line up at Middletown High School to participate in Decorated Holiday Vehicle Parade.  7:00 p.m. - Parade takes off from Middletown High School and travels through Downtown Middletown After Parade: Evening pub crawl, visiting multiple local spots throughout Downtown  What to Know A full what to bring list and all final details will be included in your reminder email sent to you a few days prior to the event. Ugly Sweater Contest Wear your ugliest holiday sweater for your chance to win a prize!

Live Music at Seaview Bistro at Water's Edge Resort & Spa

Enjoy Live Music every Friday & Saturday At Seaview Bistro At the Water's Edge Resort & Spa From 9:00 p.m. to Midnight.   Questions:  Contact Email - [email protected] 

Water's Edge Resort & Spa At Seaview Bistro 1525 Boston Post Road Westbrook, CT 06498

Holiday on Main Street presents Magic of Middletown

10:00 AM to 2:00 PM Please visit www.holidayonmain.com for all Holiday on Main Street dates and events!

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Holiday Jamboree Tea at the Westbrook Inn Bed and Breakfast

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not i......More

Enjoy a two hour tea service before the Ivoryton Holiday Jamboree. Featuring a choice of two teas, finger sandwiches, cookies, scone with jam and creme fraiche, and more!  Tickets are $40.00 per person + tax. Gratuity not included.  We are sorry but we do not issue refunds or credits. Click here to purchase your tickets. 

Westbrook Inn Bed and Breakfast 976 Boston Post Road Westbrook, CT 06498

Live Music at Seaview Bistro at Water's Edge Resort & Spa

Enjoy Live Music every Friday & Saturday At Seaview Bistro At the Water's Edge Resort & Spa From 9:00 p.m. to Midnight.   Questions:  Contact Email - [email protected] 

Water's Edge Resort & Spa At Seaview Bistro 1525 Boston Post Road Westbrook, CT 06498

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Sunday Brunch with Santa at Saybrook Point Resort & Marina

Brunch with Santa at Fresh Salt Celebrate the season with a festive family outing at Saybrook Point! Join us for Brunch with Santa, where kids can experience the magic of the holidays while enjoying delicious food and holiday cheer. Snap a photo with Santa, savor se......More

Brunch with Santa at Fresh Salt Celebrate the season with a festive family outing at Saybrook Point! Join us for Brunch with Santa, where kids can experience the magic of the holidays while enjoying delicious food and holiday cheer. Snap a photo with Santa, savor seasonal favorites, and make memories that sparkle.  

Saybrook Point Resort and Marina Fresh Salt Restaurant 2 Bridge Street Old Saybrook, CT 06475

Wesleyan Potters Annual Holiday Sale

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. ......More

Come experience the beauty of artistry and craft through exquisite handmade works in pottery, jewelry, wood, stone, glass, and fiber... each a reflection of the skill and imagination of local artists. Open daily 10:00am to 6:00pm, Black Friday through Christmas Eve. Additional free parking located in the rear - accessible from Birdsey Avenue. Bring a friend!

Wesleyan Potters 350 South Main Street Middletown, CT 06457

Gilead Mental Health Resource Center Family Support Group

Gilead’s Mental Health Resource Center is excited to launch a free open Family Support Group for those who have a loved one living with a mental health diagnosis. Watching a loved one struggle with a mental illness can be difficult. Participants will learn coping to......More

Gilead’s Mental Health Resource Center is excited to launch a free open Family Support Group for those who have a loved one living with a mental health diagnosis. Watching a loved one struggle with a mental illness can be difficult. Participants will learn coping tools, importance of self-care, peer-to-peer discussion, listen to guest speakers and learn about helpful community supports and resources.  

175 East Main St., Middletown, with the option of attending virtually. Light refreshments will be served. For more information, please call 860-530-4357 or email [email protected].