Hallmark Christmas Towns

Westbrook, CT: A Cozy Coastal Christmas

Westbrook offers a charming mix of small-town holiday spirit and coastal beauty, making it a favorite spot for a winter escape.

Holiday Events in Westbrook:

• Tree Lighting & Holiday Parade on December 8, 2024—Westbrook’s annual tree lighting at Town Green is a community favorite. The evening starts with a holiday parade featuring local groups, music, and colorful floats. It ends with the lighting of the town’s tree and a visit from Santa. The event will also have horse-drawn carriage rides and s’mores!
• Westbrook Holiday Craft Fair—This craft fair at the Westbrook Outlets is perfect for finding one-of-a-kind gifts. It showcases handmade items from local artisans, including jewelry, home decor, and holiday treats.



Where to Stay:

Westbrook Inn Bed & Breakfast – Step into history and holiday cheer at this beautifully restored 1870s inn. The Westbrook Inn Bed & Breakfast is the perfect base for your holiday adventures, offering cozy, individually decorated rooms, festive decor, and delicious homemade breakfasts. Located near the heart of Westbrook, it’s within walking distance of local holiday festivities and scenic winter walks along the shoreline.

Old Saybrook, CT: History and Holiday Cheer

Old Saybrook’s rich history and charming Main Street make it an idyllic holiday destination.

Holiday Events in Old Saybrook:

• Torchlight Parade & Tree Lighting December 14, 2024– One of the highlights of the holiday season in Old Saybrook is the annual Torchlight Parade, where the streets are illuminated by torches carried by parade-goers. This event leads into the lighting of the town’s Christmas tree at Town Green, with caroling and hot chocolate to warm your heart.
• Main Street Holiday Stroll – Stroll down Old Saybrook’s historic downtown Main Street, adorned with twinkling lights and holiday displays. You’ll find local shops offering unique gifts and holiday deals and plenty of cozy spots to stop for a warm drink.



Where to Stay:

The Stannard House Bed & Breakfast – The Stannard, formerly Captain Stannard House, is a must for those seeking a touch of history and elegance. Recently acquired by Meri Wick and Marcus Little, this charming inn will be decked out in festive, nautical-inspired holiday decor. With luxurious yet comfortable accommodations and a warm, welcoming atmosphere, it’s an ideal spot for relaxing after a day of holiday activities in Old Saybrook.

Madison, CT: A Holiday Wonderland

Madison’s picturesque setting, with its quaint shops and festive events, makes it a favorite holiday destination.

Holiday Events in Madison:

• Madison’s Holiday Lantern Parade – This beloved holiday tradition invites the community to create and carry handmade lanterns through the town, illuminating the streets as they march toward the town’s tree lighting ceremony. The event has caroling, hot cocoa, and plenty of holiday spirit.



Holiday Shopping in Madison – Explore the boutiques along Boston Post Road, many of which are festively decorated and offer special holiday items. Stop by RJ Julia Booksellers for holiday-themed storytimes and book signings—a perfect family-friendly activity!

Clinton, CT: Seaside Shopping and Holiday Fun

Clinton is the perfect spot to explore unique holiday shops and embrace the festive spirit.

Holiday Events in Clinton:

• Clinton Christmas Fair – Head to Clinton’s Town Hall for a holiday fair featuring local vendors offering everything from handmade crafts to baked goods. The festive atmosphere, complete with live music and food vendors, makes this a favorite holiday event.



Clinton Historical Society Holiday Open House – Visit Clinton’s historic homes and buildings, beautifully decorated for the holidays, and experience the charm of a bygone era during the open house event.

Transportation Ideas: Getting to the Connecticut Shoreline

If you're coming from New York City or Boston, reaching the Connecticut shoreline is easy and convenient.

From New York City:

• By Train: Hop on an Amtrak or Shore Line East train from Penn Station. The trains offer a scenic ride along the coast, dropping you off in Old Saybrook, just a short drive from Westbrook, Clinton, and Madison. Shore Line East also connects to New Haven, providing easy access to additional shoreline towns.
• By Car: Take I-95 North out of Manhattan. In just about 2 hours (depending on traffic), you’ll find yourself in the heart of the Connecticut shoreline, ready to enjoy holiday festivities.



From Boston:

• By Train: Amtrak’s Northeast Regional offers service from Boston’s South Station to Old Saybrook, with beautiful views of the coast along the way. From there, it’s easy to travel to Westbrook, Madison, or Clinton by car or local taxi service.
• By Car: Drive south on I-95 from Boston, and in about 2 hours, you’ll arrive at your holiday destination along the Connecticut shoreline.