11 of the Most Welcoming Towns in Connecticut
Aptly nicknamed the Constitution State, Connecticut is the southernmost New England state with charming cities and a rich colonial history. Nearly 60 percent of the state woodlands, which helps to keep the rural, classic feel to many of the small towns. The variety of landscapes and attractions of these welcoming towns means there is something for every traveler, ranging from oceanfront views to rolling farmlands and vineyards. For visitors who are ready to visit Connecticut but are unsure where to go, check out these 11 welcoming towns with no shortage of fun things to do. These towns offer a variety of family-friendly and individual recreational events, as well as opportunities to get out into nature and enjoy all the natural beauty Connecticut has to offer.
Putnam
Putnam, Connecticut, is a small town in the northeastern corner of the state with just over 7,000 people. The city was originally named Aspinock and was known for its once-booming mill and manufacturing industry. Putnam sits almost in the middle of the Quinebaug River's length, an impressive 69-mile river from south central Massachusetts to the Shetucket River near Norwich, Connecticut. In Putnam, one of the most charming attractions is the Putnam River Trail, a 1.8-mile path featuring several bridges that overlook the river.
Tourists from across the country travel to Putnam to experience the downtown's "Arts & Al Fresco" section, filled with antique shops, local eateries, and the iconic Bradley Playhouse theater. This historic theater has been open since 1901 and was featured on the paranormal investigation show Ghost Hunters. Today, the theater puts on several productions every year. Located close to The Bradley Theater is Jessica Tuesdays, a charming boutique restaurant that's brought unique cocktails to Putnam for years. Putnam is a welcoming small town that's an excellent destination for families with children or those looking for an upscale dining experience.
Old Lyme
For outdoor enthusiasts looking for a welcoming small town on the water, Old Lyme is a must-visit. Old Lyme is located on the Connecticut River and the Long Island Sound and has just under 7,500 residents. The town has a reputation for being an artists' community and is known best for its historic district located on Lyme Street. Visitors can explore the many exhibits at the Florence Griswold House and Museum. The museum was once the home and boardinghouse of Florence Griswold, an Old Lyme resident known as the center of the 20th-century Old Lyme Art Colony. Visiting the museum today allows one to explore the house, see numerous American Impressionist exhibits, and view more modern pieces in the Krieble Gallery.
After spending a day at the museum, stop in and meet some of the town's welcoming patrons at The Side Door Jazz Club. This unique club was featured in Downbeat Magazine's "106 Great Jazz Venues" and is an excellent spot for a night out, offering live music and delicious dinner reservation options. Another local favorite is Studio 80 + Sculpture Grounds, which is located conveniently on Lyme Street. This outdoor attraction has over 4 acres of landscaped space featuring 66 contemporary sculptures from artist Gilbert Boro.
Westport
Want a vacation spot in Connecticut with ocean views and upscale attractions? Westport is a prime tourist destination in the state and is often called an affluent suburb. This welcoming town has the most ocean and riverfront in the state, meaning there is no shortage of opportunities to spend a day on the water. Westport is located in Fairfield County between Norwalk and Fairfield and has an impressive population of around 28,000. If you're visiting Westport during the summer, the Levitt Pavilion for the Performing Arts is an outdoor amphitheater that puts on live music shows and community events. It's a great place to meet some of the town's locals and enjoy the onsite concessions.
Another excellent summertime attraction is Sherwood Island State Park on the Sherwood Island Connector in Westport. Sherwood Island State Park is Connecticut's oldest state park, with over 200 acres of land for visitors to enjoy. There are designated spots for fishing and swimming, a picnic grove, and unique wetlands. Westport is also home to the Westport Country Playhouse, a historic theater in a renovated 1830s tannery. The productions from this theater are highly rated, and shows run year-round. After watching some of the best local performers, stop for a meal or cocktail at Gabriele's of Westport, just down the road from the theater.
Cheshire
Cheshire is a moderately-sized town in New Haven County that has a population of roughly 29,000 people. This charming town has some unique attractions not found in other areas of Connecticut and, interestingly, is known as "The Bedding Plant Capital of Connecticut." One of the best things about Cheshire is that the town takes pride in keeping an authentic small town with all of the charm of an old New England area. History buffs visiting Cheshire should stop at the Lock 12 Historical Park. This attraction is a park and museum with hiking trails on the site of a restored section of Farmington Canal.
Located close to the park is Cheshire Coffee, a locally owned cafe that has served delicious coffee and pastries since 2009. However, Cheshire Coffee is just one of many dining establishments in Cheshire, as Viron Rondo Osteria and Vespucci's Restaurant are also popular Italian restaurants in the town. Families with kids or those who enjoy antiquing and lobbying can't miss out on seeing the Barker Character Comic and Cartoon Museum. This museum offers tours highlighting the incredible collection of antique toys dating back nearly 150 years.
Wallingford
Another welcoming town in New Haven County is Wallingford. Between New Haven and Hartford, Wallingford has a large population of 45,000 yet still manages to feel like a classic New England town. Wallingford has many vineyards and wineries, downtown restaurants and shopping, and breweries, making this an ideal destination for individuals and families. The town is part of the Connecticut Wine Trail. It has Paradise Hills Vineyard & Winery and Gouveia Vineyards as prime locations to visit out of the 45 establishments listed in the collection. Both Wallingford vineyards have tasting rooms, tours, and incredible scenic views.
There is no shortage of fun and welcoming attractions in Wallingford! One popular spot for music enthusiasts is the Toyota Oakdale Theatre. This venue is a town staple that seats 4,500 and features big bands and smaller performances, making it a truly versatile location. The Redwood Country Flea Market is an excellent visit for antiquers, and it even has the DJM Redwood Grill & Pizza restaurant on site. If you're visiting Wallingford during the fall, the Trail of Terror haunted attraction should be on your bucket list. This haunted trail has over 80 dedicated scare actors waiting for guests who are brave enough to enter the gates.
Farmington
Farmington is a town with 25,000 people that sits in Hartford County. This town gained its name from being located inside a farming area of the state but gained the nickname "mother state" because it was large enough to be split into nine communities. Farmington sits on the Farmington River and has a rich colonial history proudly displayed in the town's historic district. It's also known that George Washington passed through the town during Revolutionary War times, referring to it as the "village of pretty houses." Farmington is known for its low crime rate and abundance of nature attractions.
Are you looking for a quiet day in Farmington? The Hill-Stead Museum is a great spot to take in French Impressionist artwork and see the 1901 Colonial Revival-style home. The museum has guided tours and allows guests to explore the beautifully manicured 152-acre property filled with historic structures and gardens. If you're in Farmington, don't forget to get out in the fresh air for a walk or bike ride on a portion of the Farmington Canal Heritage Trail. This well-kept rail trail has over 48 miles that run from New Haven, Connecticut, to the Massachusetts border!
Niantic
Located halfway between New York and Boston, Niantic is a bayside Connecticut town with a little over 3,000 residents. One of the best things about Niantic is that it seems to have countless outdoor areas with ocean views, kid-friendly museums, and a main street lined with shops and restaurants. Downtown Niantic is also known for its festive events, including the Niantic Light Parade that's run for over 35 years every December. The Niantic Winters Farmers Market is another welcoming place for locals and tourists, as it offers an option to visit the town's vendors indoors for the winter season.
If visiting Niantic during the warmer months, there is an excellent selection of state parks and beaches to explore. Harkness Memorial State Park is a historical preservation perfect for a day trip. This park sits on the Long Island Sound and is on the grounds of a botanical garden and Renaissance Revival mansion built in 1906. The Niantic Children's Museum is another popular destination that opened in 1992 and now offers 5,000 square feet of interactive learning for kids aged nine and under. The museum has workshops, live animal events, and year-round science activities.
Essex
Middlesex County, Essex, is a small town referred to as a "Perfect Small American Town" in the 1000 Places to See Before You Die travel guide. The town's proximity to the Long Island Sound gives Essex a coastal feel while keeping the rural charm many New England towns are known for. There's no doubt the Connecticut River Museum is one of the most popular areas in Essex that was first established in 1974. Today, the museum has tours that bring visitors to the river and events throughout the year that teach the history of the Connecticut River. The museum also has open ground on the water where visitors can walk while overlooking the harbor.
Another well-known location in Essex is the Essex Steam Train & Riverboat, founded in 1868. No matter your interests, the Essex Steam Train & Riverboat has numerous great experiences for all ages. A railbike system open during the warmer months offers an 8-mile scenic trip, train & riverboat rides, and the iconic Christmas 'North Pole Express' experience. After a day of fun, don't miss out on a chance to eat at The Griswold Inn, a historic hotel and restaurant dating back to 1776.
Madison
For folks looking for a small, welcoming Connecticut town that feels like it's straight out of a movie during the fall season, Madison checks all the boxes. Madison has population of around 18,000 and is also home to the respected R.J. Julia Booksellers, an award-winning, locally-owned bookstore. The English settled the town in 1641 officially incorporated in 1826, lending to its rich history. Modern Madison is a pedestrian-friendly area with small shops, cafes, and boutiques lining the streets.
The Meigs Point Nature Center is a fun outdoor location in Madison that is a free attraction that's great for all ages. The nature center is located at Hammonasset Beach State Park and has interactive events, touch tanks, and live animal exhibits that are fun and informative. Another great spot to visit after a day in nature is the Clinton Premium Outlets. This shopping center has numerous outlet stores and dining options to close your day with a delicious meal.
Chaplin
Chaplin is a tiny Connecticut town in Windham County that has a population of just over 2,000 people. The rural town has a unique history in that it was developed in an area previously unsettled and went on to keep some of the original architecture and designs from the early 1800s. It's known best for its hidden nature attractions and stunning natural landmarks, with people traveling from all over the state to visit Diana's Pool. Diana's Pool is a portion of the Natchaug River that formed into a swimming hole filled with beauty and is featured in some local town legends.
The James L Goodwin State Forest is located in Chapin and has over 2,000 acres dedicated to year-round activities. This state forest has an educational nature center, numerous hiking trails, and three different ponds where visitors can sit and have a picnic while enjoying the views or fishing. Part of Natchaug State Forest lies in Chaplin and is known for horse-friendly hiking trails and stone structure picnic sites. There are also camping facilities available and opportunities for fishing.
Mystic
One of the more unique and one-of-a-kind towns in Connecticut is Mystic. Mystic is a tiny village town between Stonington and Groton and has a history of shipmaking. While Mystic is a coastal town, there's no bad season to visit! There are numerous shops and events that are open year-round and give a glimpse into life in this idyllic village. To start, no trip to Mystic is complete without visiting the Mystic Aquarium. There are few aquariums in the state as elaborate or well-developed as Mystic Aquarium, as it has thousands of different species of marine animals.
Another must-see location in Mystic is the Mystic Seaport Museum. This museum is the biggest maritime museum in the US and is home to 4 national historic landmark ship vessels! It's the perfect day trip for the history enthusiast or anyone who wants to learn more about this landmark seaport village. Olde Mystic Village is an excellent spot the whole family can enjoy open year-round. This outdoor shopping center has over 50 stores set in a colonial atmosphere, making it a truly unique destination in Mystic.
Connecticut is rich in history, natural beauty, and fun attractions. Whether it's learning about the maritime heritage of Mystic or taking a moment to relax in the wild landscapes of Chaplin, there's a town in Connecticut sure to welcome you with open arms. Plan your next vacation to one of these quaint towns in Connecticut and take in all this region has to offer.
