Connecticut’s charming small towns offer the perfect escape for a weekend getaway. From coastal gems to historic districts, you’ll find a wealth of experiences waiting to be discovered. These best towns in Connecticut provide a unique blend of natural beauty, rich history, and local culture that will captivate your senses and leave you wanting more.
As you plan your trip, you’ll want to explore the quaint villages, scenic landscapes, and hidden treasures that make Connecticut so special. Whether you’re interested in browsing antique shops, enjoying outdoor activities, or simply soaking in the atmosphere of picturesque coastal towns, there’s something for everyone. Get ready to uncover the charm and character of Connecticut’s most delightful small towns on your next weekend adventure.
Stonington Borough: A Quaint Coastal Village
Nestled between New York and Boston, Stonington Borough offers a charming escape from the hustle and bustle of big cities. This picturesque coastal village, settled in 1752, has earned its place as one of the Top 10 prettiest coastal towns in New England, according to Yankee Magazine. As you explore this mile-long peninsula, you’ll discover a perfect blend of history, natural beauty, and small-town charm.
Stonington’s Historic District
Step back in time as you wander through Stonington’s well-preserved historic district. The area boasts an impressive collection of 18th and 19th-century buildings, showcasing colonial, Federal, and Greek revival architecture. To delve deeper into the town’s rich maritime history, visit the Old Lighthouse Museum, dating back to 1840. For a panoramic view of three states, climb to the top of this iconic landmark.
Adjacent to the lighthouse, you’ll find the Nathaniel B Palmer House, a colossal Victorian mansion overlooking Stonington harbor. This beautifully preserved home offers a glimpse into 19th-century life with its period furnishings and artifacts.
Stonington’s Waterfront
The borough’s waterfront is a hub of activity and natural beauty. Take a leisurely stroll along the docks, admiring the boats and soaking in the stunning views of Fisher’s Island Sound and Little Narragansett Bay. For beach lovers, DuBois Beach offers a secluded spot to enjoy swimming, sunbathing, and relaxation.
Water enthusiasts will find plenty of activities to enjoy, including boating, fishing, kayaking, and paddleboarding. The sheltered waters make Stonington a major yachting center and home to Connecticut’s last remaining fishing and lobstering fleets, ensuring access to the freshest seafood.
Stonington’s Culinary Scene
Your taste buds are in for a treat in Stonington Borough. The village boasts a thriving culinary scene, with options ranging from casual seafood shacks to upscale dining establishments. Many restaurants highlight the region’s abundant local produce and seafood, offering a true farm-to-table experience.
For a memorable dining experience with a view, head to the Dog Watch Café. This waterfront eatery serves up delicious sandwiches and seafood while treating you to stunning sunset views over the harbor. Don’t miss their outdoor bar, “The Dog Pound,” for drinks and live music from May through October.
As you explore Water Street, you’ll find an array of eclectic shops, art galleries, and boutiques. The borough also hosts year-round events, including concerts, lectures, garden tours, parades, and farmers’ markets, adding to its vibrant community atmosphere.
Wethersfield: Connecticut’s Most Ancient Town
Step back in time as you explore Wethersfield, Connecticut’s oldest town, with a rich history dating back to 1634. This charming destination offers you a unique blend of colonial-era architecture, fascinating museums, and scenic natural beauty. As you wander through its streets, you’ll discover why Wethersfield is a must-visit for history buffs and nature lovers alike.
Wethersfield’s Historic Old Town
As you stroll through the Historic Old Town district, you’ll be transported to a bygone era. With over 150 homes predating the Civil War, and many even older than the Revolutionary War, this area boasts the largest historic district in Connecticut. The quiet streets, lined with brick-paver sidewalks and shaded by mature trees, create an atmosphere that’s a world apart from the nearby bustle of I-91.
Begin your journey at the Broad Street Green, a picturesque park that once served as grazing land for early settlers’ livestock. Today, it’s home to magnificent specimen trees, including elms, oaks, sycamores, and a copper beech dating back to 1836. Some of these towering giants reach heights of up to 15 stories, creating a stunning natural canopy.
As you explore further, you’ll come across the Ancient Burying Ground, where headstones dating back to 1648 tell poignant tales of the town’s early inhabitants. The inscriptions on these stones showcase the craftsmanship of a dozen different Connecticut Valley stone carvers, offering a unique glimpse into the area’s history.
Wethersfield’s Webb-Deane-Stevens Museum
No visit to Wethersfield is complete without a tour of the Webb-Deane-Stevens Museum. This remarkable complex consists of three historic houses that provide an immersive experience of 18th-century life in Wethersfield.
The Joseph Webb House, built in 1752, is a National Historic Landmark and famously hosted George Washington during his visits to the town. As you tour the house, your guide will reveal fascinating stories behind the elaborate wall murals installed in 1916 by Wallace Nutting, a renowned photographer and artist who purchased the home as a backdrop for his work.
Next, you’ll explore the Silas Deane House, another National Historic Landmark dating back to 1770. This Georgian-style home reflects the refined taste of America’s first diplomat to France, with its finely appointed interior offering a glimpse into the life of the upper class during that era.
The third home in the complex, the Isaac Stevens House, provides a contrast to the more aristocratic residences. Built in the early 1800s, this house offers insight into the life of a tanner and features a collection of period children’s toys displayed in a second-floor bedroom.
Wethersfield Cove
To round out your visit, head to Wethersfield Cove, a picturesque spot along the Connecticut River. This natural harbor, once an oxbow of the “Great Tidal River,” played a crucial role in the town’s maritime history. Today, it’s a popular destination for outdoor enthusiasts, offering opportunities for boating, fishing, and birdwatching.
At the cove, you’ll find a public boat launch providing access to the Connecticut River. The area also features a park with open spaces perfect for picnicking or simply enjoying the waterfront views. Don’t miss the historic warehouse on the cove’s banks, now housing a Wethersfield Historical Society maritime exhibit. This building serves as a reminder of the thriving West Indies trade that flourished in Wethersfield from 1650 to 1830.
Sharon: A Tranquil Countryside Retreat
Nestled in the heart of New England, Sharon offers you a serene escape from the hustle and bustle of city life. This charming town, situated in the northwest corner of Litchfield County along the New York border, boasts a picturesque landscape of rolling hills, open farmland, and breathtaking vistas that seem to stretch endlessly.
As you approach Sharon, you’ll be greeted by a quintessential New England scene: a town green that could have been plucked straight from a Norman Rockwell painting. The diminutive downtown may be small, but it’s brimming with character and history.
Sharon’s Hiking Trails
For outdoor enthusiasts, Sharon is a paradise waiting to be explored. The Sharon Land Trust manages over 800 acres of land open to public use, offering some of the best hiking in Litchfield County, if not all of Connecticut. As you traverse the trails, you’ll be treated to picturesque views, lush forests, blooming flowers, and diverse wildlife.
The hiking trails cater to various skill levels, ranging from easy strolls to moderate hikes with challenging uphill sections. Some trails are even maintained for horseback riding, adding another dimension to your outdoor adventures. As you explore, remember to follow the trail guidelines:
- Keep dogs on a leash and clean up after them
- Practice “Leave No Trace” principles
- Respect private property and stay on marked trails
- Be aware of wildlife, including bears, snakes, and ticks
Sharon’s Historic Sites
Step back in time as you explore Sharon’s rich history. The town’s historic district showcases well-preserved 18th and 19th-century buildings, offering a glimpse into the area’s past. One must-visit location is the Sharon Historical Society Museum, housed in a 1775 building listed on the National Register of Historic Places. Located at 18 Main St. (Route 41), the museum features changing history exhibits, an art gallery, and a hands-on History room perfect for family learning.
As you wander through town, you’ll notice the influence of both long-time residents and newcomers who have banded together to preserve and enhance Sharon’s charm. Keep an eye out for public art murals sponsored by local businesses, adding a contemporary flair to the historic backdrop.
Sharon’s Farm-to-Table Experiences
Sharon’s agricultural heritage is alive and thriving, offering you a chance to savor the flavors of the land. The town is home to several local farms and producers that provide a variety of fresh, locally-sourced products. From crisp vegetables and creamy dairy to succulent meats and artisanal baked goods, you’ll find an array of farm-to-table delights.
To truly immerse yourself in Sharon’s culinary scene, visit the local farmers’ markets or farm stands. Here, you can interact directly with the producers and learn about their sustainable farming practices. Some farms even offer tours or pick-your-own experiences, allowing you to connect more deeply with the source of your food.
As you explore Sharon, you’ll discover a town that seamlessly blends natural beauty, rich history, and a thriving local food scene. Whether you’re hiking through lush forests, exploring historic sites, or savoring farm-fresh cuisine, Sharon offers a tranquil countryside retreat that will leave you refreshed and inspired.
PLAN A TRIP TO CONNECTICUT’S SMALL TOWNS
Putnam: An Antique Lover’s Dream
Nestled in the heart of Connecticut, Putnam offers you a charming escape filled with unique treasures and cultural experiences. This small town has become a destination for antique enthusiasts and art lovers alike, boasting a vibrant downtown area that’s brimming with character and history.
Putnam’s Antique Shops
As you stroll through Putnam’s downtown, you’ll find yourself surrounded by an abundance of antique shops. Each store is a treasure trove waiting to be explored, offering a diverse array of vintage finds and unique pieces. From furniture and home decor to collectibles and curiosities, you’re sure to discover something special that catches your eye.
The antique shopping experience in Putnam is more than just a pastime; it’s an adventure. You’ll have the opportunity to browse through carefully curated collections, each item with its own story to tell. Whether you’re a seasoned collector or a casual browser, the friendly shop owners are always ready to share their knowledge and help you find that perfect piece.
Putnam’s Arts Scene
Beyond its reputation for antiques, Putnam boasts a thriving arts community that adds to its cultural allure. The town is home to several galleries and studios showcasing the work of local and regional artists. As you explore, you’ll encounter a diverse range of mediums, from painting and sculpture to pottery and jewelry making.
The Putnam Arts Council (PAC) plays a crucial role in nurturing this creative environment. Their mission is to grow and support the creative and cultural sectors, benefiting the community and economy. The PAC promotes local artists, supports cultural events, and works to increase access to the arts for the Greater Putnam community.
One notable venue is the Silver Circle Gallery & Art Center, located in the historic district of downtown Putnam. This gallery serves as a hub for artistic expression and appreciation, offering a glimpse into the vibrant creativity that flourishes in this small New England town.
Putnam’s Outdoor Recreation
While Putnam is renowned for its antiques and arts, it also offers plenty of opportunities for outdoor enthusiasts. The town’s location along the Quinebaug River provides ample chances for fishing, kayaking, and other water-based activities. You can spend a relaxing afternoon by the river, enjoying the scenic views and peaceful atmosphere.
For those who prefer land-based adventures, nearby hiking trails and parks offer scenic vistas and opportunities for outdoor exploration. These natural spaces provide a perfect complement to the town’s cultural offerings, allowing you to balance your antiquing and art appreciation with some fresh air and exercise.
Throughout the year, Putnam hosts a variety of events that showcase its vibrant community spirit. From the Fire & Ice Festival to the Pumpkin Festival, there’s always something happening in this lively town. These events, organized by local groups like the Putnam Business Association and the Putnam Arts Council, keep the community vibrant and welcoming for both locals and visitors.
As you explore Putnam, you’ll quickly understand why it’s been recognized as one of the top small towns to visit. Its unique blend of antique shops, thriving arts scene, and outdoor recreation opportunities create an inviting atmosphere that’s hard to resist. Whether you’re searching for a rare antique, admiring local artwork, or simply enjoying the town’s natural beauty, Putnam offers a memorable experience that will leave you wanting to return.
Essex: A Perfect River Valley Getaway
Nestled along the picturesque Connecticut River, Essex offers you a charming escape that combines history, natural beauty, and unique attractions. This quaint town, often referred to as “The Best Small Town in America,” is actually composed of three distinct villages: Essex Village, Ivoryton Village, and Centerbrook. Each area contributes to the town’s overall appeal, making it an ideal destination for a perfect river valley getaway.
Essex’s Main Street
As you stroll down Essex’s Main Street, you’ll find yourself transported to a bygone era. The street is lined with well-preserved historic buildings that house an array of boutiques, restaurants, and local businesses. This walkable downtown area creates a picturesque setting that invites you to explore at a leisurely pace.
The charm of Essex’s Main Street lies in its ability to blend the past with the present. You can browse unique shops, savor local cuisine, or simply admire the architecture that tells the story of this riverside town. The area’s welcoming atmosphere and scenic beauty make it a perfect spot for a relaxing afternoon walk or an evening out.
Essex Steam Train and Riverboat
One of the top attractions in Essex is the Essex Steam Train and Riverboat, located just over a mile from the town center. This unique experience has been delighting visitors since 1971 and offers you a chance to step back in time while enjoying the natural beauty of the Connecticut River Valley.
Your journey begins at the historic 1892 Essex Station, where you’ll board a vintage coach pulled by a steam locomotive. The 2.5-hour round trip takes you on a 12-mile narrated excursion through the quintessential New England towns of Deep River and Chester. Along the way, you’ll have the opportunity to:
- Observe diverse wildlife in their natural habitats
- Pass by tidal wetlands and preserves
- Enjoy scenic views of the Connecticut River
At Deep River Landing, you’ll transfer to the Becky Thatcher riverboat for a 1.25-hour cruise along the Connecticut River. From the boat’s multiple decks, you can take in breathtaking views of:
- Deep water coves and inlets
- Lush marshes
- Rocky shorelines
- Historic sites such as Gillette Castle and Goodspeed Opera House
This combination of train and riverboat offers a unique perspective on the region’s natural beauty and rich history, making it a must-do activity during your visit to Essex.
Essex’s Connecticut River Museum
To delve deeper into the area’s history and culture, a visit to the Essex Connecticut River Museum is essential. This institution celebrates the art, history, and nature of the Connecticut River Valley, offering you a comprehensive look at the region’s heritage.
Located right on the riverfront, the museum provides interactive exhibits, educational programs, and stunning views of the Connecticut River. You can explore displays that showcase:
- The region’s maritime history
- Local ecology and wildlife
- Art inspired by the Connecticut River Valley
The museum serves as a gateway to understanding the importance of the river in shaping the area’s development and culture. Its exhibits and programs offer insights into both the past and present of this beautiful river valley.
As you explore Essex, you’ll discover a town that seamlessly blends natural beauty, rich history, and unique attractions. Whether you’re wandering down Main Street, embarking on a scenic journey aboard the Essex Steam Train and Riverboat, or learning about the region’s heritage at the Connecticut River Museum, Essex offers a perfect river valley getaway that will leave you with lasting memories.
Milford: A Charming Coastal Community
Nestled along the picturesque Connecticut coastline, Milford offers you a delightful blend of natural beauty, rich history, and coastal charm. This enchanting town is known for its stunning beaches, well-preserved historic district, and abundant outdoor recreational opportunities. As you explore Milford, you’ll discover why it’s become a favorite destination for both locals and visitors alike.
Milford’s Beaches
Milford boasts several beautiful beaches that provide the perfect setting for a relaxing day by the water. You’ll find plenty of opportunities for swimming, sunbathing, and beachcombing along the town’s scenic shoreline. Walnut Beach is a popular spot where you can enjoy the sun and surf while taking in breathtaking views of Long Island Sound.
For a unique coastal experience, head to Silver Sands State Park. Here, you’ll discover a fascinating natural phenomenon known as a tombolo – a sand bar that connects the mainland to Charles Island. At low tide, you can walk along this sandy path to explore the island. However, it’s crucial to check the tide schedules before venturing out, as the incoming tide can quickly submerge the tombolo, creating dangerous conditions.
Milford’s Historic District
As you stroll through downtown Milford, you’ll be transported back in time. The town boasts three contiguous National Register Historic Districts: North Milford, Victorian, and Shipyard Historic Districts, all added to the National Register of Historic Places in 1983. Within just 20 blocks, you’ll encounter more than 50 Victorian buildings dating from 1814 to 1914, each showcasing a variety of architectural styles including Gothic, Italianate, Second Empire, and Queen Anne.
The heart of the community is the Milford Green, a charming central park surrounded by these well-preserved 19th-century buildings. This historic area serves as a hub for community gatherings and events, offering a glimpse into Milford’s rich past while providing a vibrant present-day atmosphere.
Milford’s Silver Sands State Park
Silver Sands State Park is a true gem of Milford, offering a diverse range of natural attractions and recreational activities. Located along the Long Island Sound, this park provides you with access to a beautiful beach, hiking trails, and excellent birdwatching opportunities.
As you explore the park, you’ll find:
- Two miles of walking trails, boardwalks, and bridges that take you through various terrains, including wetlands, beaches, and coastal forests.
- A 1.5-mile out-and-back trail across the tombolo to Charles Island, where you can catch a glimpse of the ruins from a former resort and religious retreat.
- A two-mile boardwalk offering stunning views of Long Island Sound and Charles Island, as well as up-close looks at the park’s restored tidal marsh and impressive dunes.
Silver Sands State Park is also a haven for wildlife enthusiasts. Over 200 species of birds migrate to the park each year, making it one of the three largest wading bird rookeries in the state. The park is designated as a Natural Area Preserve, Long Island Sound Stewardship Site, and Audubon Important Bird Area (IBA).
For fishing enthusiasts, the park offers ample opportunities to cast a line. You can fish throughout the park, including from the tombolo extending to Charles Island. Popular catches include bluefish, striped bass, summer flounder, hickory shad, and weakfish.
Conclusion
Connecticut’s charming small towns offer a perfect blend of history, natural beauty, and unique experiences for weekend getaways. From coastal gems like Stonington and Milford to inland treasures like Wethersfield and Sharon, each destination has its own character and attractions to explore. These towns showcase Connecticut’s rich heritage, picturesque landscapes, and vibrant local cultures, providing visitors with countless opportunities to create lasting memories.
Whether you’re interested in antique hunting in Putnam, riding a steam train in Essex, or hiking through scenic trails in Sharon, Connecticut’s best towns have something for everyone. The state’s diverse offerings allow travelers to tailor their trips to their interests, be it history, outdoor adventures, or culinary experiences. By visiting these enchanting locales, you’ll gain a deeper appreciation for Connecticut’s unique charm and leave with a desire to return and discover more of what the Nutmeg State has to offer.
FAQs
Q: What are some recommended destinations for a weekend trip in Connecticut?
A: For an ideal weekend getaway in Connecticut, consider visiting these top locations:
- Mystic – Known for its captivating maritime charm.
- Old Saybrook – A quintessence of New England charm.
- Stonington – A beautiful coastal town near Long Island Sound and Mystic River.
- Simsbury – Notable for its scenic beauty and historical sites.
- Madison – Known for its lovely beaches and community atmosphere.
- Greenwich – Offers a mix of upscale attractions and natural beauty.
- New Haven – Rich in cultural and educational attractions.
- Hartford – The state’s capital with numerous historical and cultural sites.
Q: Which town in Connecticut is considered the most beautiful?
A: Connecticut boasts several beautiful towns. Some of the most picturesque include Milford, Essex, Greenwich, Old Saybrook, Westport, Wethersfield, Madison, and Old Lyme, the latter known for its artistic heritage and scenic beaches.
Q: What is the top tourist destination in Connecticut?
A: The Mystic Seaport Museum, the largest maritime museum in the United States, is the most visited attraction in Connecticut.
Q: What are the top attractions to visit in Connecticut?
A: Connecticut offers a variety of attractions suitable for all interests:
- Mystic Seaport Museum – A prominent history museum.
- The Mark Twain House & Museum – A historic site dedicated to the famous author.
- Foxwoods Resort Casino – A large casino with entertainment options.
- Mystic Aquarium – Known for its marine exhibits and conservation efforts.
- Yale University Art Gallery – A notable art museum.
- Olde Mistick Village – A charming shopping and dining area.
- Gillette Castle State Park – Offers hiking and historical exploration.
- Mystic Dark Room – An intimate venue for performance arts.