I spent the first 20 years of my life growing up on the Connecticut shoreline and hoping to leave. I spent the last twenty years of my life in a rare state of Yankee nostalgia for my home state. The smell of Rosa rugosa, those wrinkled rose beach flowers, sailboats dotting every shoreline, proud American flags raised on every home, quaint marinas hugging each coastal town, churches with tall white steeples poking high reminding us of our Puritan heritage, wild ungroomed beaches, miles of untouched woods, rolling green pastures with perfectly fit stone walls, lobster roll shacks, blazing fire cracker colored leaves, fog so thick you can’t see a foot in front of you, friendly people offering a hello and wave. These are the images of small town Connecticut that waver in my mind and lure me back to the Nutmeg State.
“Autumn carries more gold in its pocket than all the other seasons.” – Jim Bishop
After a decade in Washington, DC and now over a decade in Los Angeles, visits home to the Constitution State sadly have dwindled, but a scent can conjure up adolescent memories making me crave these distant idyllic moments of New England charm, where life always seems simpler. The small towns that dot Connecticut have somehow managed to preserve their Americana feel, which is so hard to find these days.
As fall brings crisp air, it also brings brilliant foliage bursting throughout New England, and there is no better time to go leaf peeping – a term my Minnesota born husband finds amusing since he never heard of such a thing until he met me. In northern New England the first scarlets and golds appear in mid-September, while the “peak” colors head south thereafter.
Tip: The Connecticut River, starting at the mouth of the Long Island Sound (between Old Lyme and Old Saybrook) and going up towards East Haddam, holds the foliage the longest, even into the first week or so of November.
Across the state you can find a diverse range of destinations and attractions with unique vantage points to leap peep. If you can, plan your trip mid week when the roads are quieter. Sometimes the best sights are discovered off the beaten path. Hiking or kayaking will help you absorb nature and truly enjoy the vibrant colors. Fall in Connecticut is not to be missed.
Experience autumn beauty in Connecticut
Planes, Trains and Automobiles
The historic Essex Steam Train and River Boat Ride choo choos you out of Essex on a 12 mile ride with scenic views of the Connecticut River up to Chester. The river boat brings you up the Connecticut River to the East Haddam Swing Bridge and then back to the Deep River Landing. Pass the Goodspeed Opera House and Gilette Castle all while gazing at the spectacular foliage views. River Quest, a company out of Haddam offers special foliage cruises along the Connecticut River too. Another option is an hour and a half train ride out of Thomaston to admire the fall foliage with the Railroad Museum of New England.
Sip and savor New England charm on the Connecticut Wine Trail with 25 wineries divided into two sections. Both the Litchfield Hills and the Southeast Corridor offer enough stops for a jovial time. Our personal favorites include Clinton’s Chamard Vineyards and Jonathan Edwards Winery in North Stonington. Reservations are not necessary. Find a designated driver or hire Gateway Limousines, Hunter Limousines, or Regency Wine Tours to make your journey smooth.
Drive scenic State Route 169 parallel to the Rhode Island border, with picturesque villages such as Canterbury, Pomfret, Brooklyn, and Woodstock. Stop for antiques along your leaf peeping escape. Stay at the stately Inn at Woodstock Hill from 1816 for the utmost relaxation with their gas fireplaces and poster beds.
Gain a new perspective on fall foliage and charter a Cessna from Chester Charter or a dazzling helicopter ride with Air Ocean Aviation where you can customize your ride with the shoreline, fall leaves, or even New York City.
How ‘bout them apples?
Pick your own apples in Guilford at Bishop’s Orchard with over twenty varieties to suit your needs. Take home some apple cider, sip vino at their winery, or buy one of their other farm fresh products at the market. In South Glastonbury, pick apples at Belltown Hill Orchards or sample local produce at their market, as well as fresh baked pie, apple cider donuts, and their famous hot apple fritters.
In Old Mystic, visit B.F. Clyde’s Cider Mill, family owned and run since 1881. Watch a cider making demonstration at the oldest steam powered cider mill. Step back in time while savoring hard and sweet ciders, apple wines, and tasty fall treats like apple pies, pumpkin breads, candy apples, kettle corn, Indian corn, and those yummy apple cider donuts. Head to Connecticut’s own Apple Harvest Festival in Glastonbury with over a hundred vendors, amusement rides, fireworks, a pub, food trucks, a 5K run and kid’s fun run all on festival grounds.
Connect with nature
Experience scenic country views in Griswold, Connecticut at Buttonwood Farm with farm fresh homemade ice cream, waffle cones, and whipped cream. Look online to see when they offer pumpkin patches and hayrides.
Kayak, canoe, SUP over even tube over a carpet of brightly colored leaves or marvel at all the leaves aflame hanging overhead on the Farmington River in New Hartford. Other paddling options include the Housatonic River in West Cornwall or the Naugatuck River in Oakville.
Cruise by the Thimble Islands off of Branford leaving from the enclave of Stony Creek. Hop aboard one of several tour boats and learn about the islands’ historical significance.
On the shoreline Rocky Neck State Park in East Lyme offers hiking trails that head straight to the beach. Bring a picnic and hike in from Route 156. Devil’s Hopyard in East Haddam offers a vista overlooking the treetops.
Take a short hike in Mt. Tom State Park in Litchfield for one of the best views in the state. The 34 foot stone tower on top of Mount Tom provides 360 degree views of the surrounding area and distant landmarks. Step back in time and spend a weekend in Litchfield’s charming Tollgate Hill Inn. Built in 1745, the colonial inn is also open for dinner and cocktails.
Hike 1.25 miles in Simsbury, CT to the 165-foot Heublein Tower in Talcott Mountain State Park. Bring a picnic and explore the former summer home of a prominent Hartford Family.
Hike or bike in the ‘Last Green Valley,’ the 35-town National Heritage Corridor in the northeast corner of the state: 5 state parks, 7 state forests, 80 ponds and lakes, and 130 miles of trails, including the East Coast Greenway. The Last Green Valley is considered the most rural area in the corridor between Boston and Washington, DC.
A series of rail trails, including the Air Line Trail North and the Hop River Trail, run through this region connecting historic mill towns like Willimantic and pass through forests and farmlands between. In the western half of the state, the Greenway connects the major cities of Hartford, New Haven, Bridgeport, and Stamford and allows users to experience history while touring the Farmington Canal Greenway from Simsbury to New Haven. Southwest of New Haven along Long Island Sound, the interim on-road route hugs the shore through the suburbs to the New York line.
Explore small towns
Most towns in Connecticut have quiet endearing main streets. You will often find a quaint inn or bed and breakfast, a town church, library, and town hall. Food choices range from outstanding delis, farm fresh goods, authentic Italian food, homemade ice ream, and lobster shacks. Notable towns include Old Lyme, Old Saybrook, Madison, Essex, Cheshire, Mystic, Stonington Borough, Westport, Greenwich, New Canaan, Litchfield, and West Hartford.
Head to Essex, New England’s perfect small town village that sits on a harbor with a main street of village shops and Colonial and Federal-era homes. A stop for a beer or a meal at ‘The Gris’ is a must. Since 1776 the Griswold Inn has entertained guests and was even captured by the British and used as a base of operations during the War of 1812. The inn was recently mentioned in the show Mad Men as a romantic weekend getaway. More nautical food and drink options can be found just down the road at the Black Seal. Nearby in the cozy town center of Chester, the River Tavern has become a popular spot due to their innovative fresh cuisine.
Walk around Mystic’s Historic District with quaint shops and a drawbridge. Eat at Mystic Pizza (think Julia Roberts), and enjoy Mystic Seaport with its 19thcentury seafaring village and home to the Charles W. Morgan, the only surviving wooden whale ship. Sleep at the Whitehall Mansion Inn with its deep history. The inn was actually moved to its present location. Best yet are the rumors of spirits to kick off an intriguing fall weekend.
Old Lyme’s historic district boasts a thriving art community still today. Once an artists’ colony, art can still be found in and around town at the Lyme Art Association, the Cooley Gallery, Florence Griswold Museum, and the Lyme Academy of Fine Arts. Twenty-seven miles of shoreline, tidal marsh, inland wetlands, and numerous waterways run throughout the town making Old Lyme a picturesque place to visit in autumn. Get cozy at the Bee and Thistle Inn or the Old Lyme Inn where you can take home those falling colorful leaves as a souvenir.
Purchase tickets ahead of time for the Glass House in New Canaan. This modernist structure was designed by architect Philip Johnson and even more splendid when the leaves have turned to fiery hues.
Tailgate Ivy League style
What is fall without football and tailgating? Wear your navy and white. People watch and cheer for the Old Blue at the 100++ season of the Yale Bowl in New Haven. Yale’s football program is one of the oldest in the world beginning in 1872.