The area known as the Connecticut River Valley that ends where the Connecticut River meets the Long Island Sound is made up of a string small towns that are big on charm and history.
The area has many historical family friendly attractions to enjoy in the summer months and some all year-round.
Top 7 Historical Attractions to Visit Along the Connecticut River Valley
1. Mark Twain Museum – Hartford, CT
The Mark Twain House is the 25-room Victorian home turned museum where American author, Samuel Clemens (Mark Twain), lived with his family from 1874 to 1891 and wrote his famous novels The Adventures of Tom Sawyer and Adventures of Huckleberry Finn.
Open Daily. 9:30-5:30 (in March, closed on Tue. and open at 11 a.m. on Sun.)
2. Gillette Castle – East Haddam, CT
Americans fought bravely for their independence from British aristocratic rule but that doesn’t mean they aren’t obsessed with castles. William Hooker Gillette, a successful actor best know for his stage and film portrayals of Sherlock Holmes, built his own on 182 acres land he called The Seven Sisters. Now referred to as Gillette Castle, visitors can look around the uniquely styled mansion that curiously looks like the set of a Sherlock Holmes mystery.
Open Memorial Day – Columbus Day, daily 10-5
3. Ivoryton Playhouse – Ivoryton, CT
Originally built in 1911 as a movie house for local factory workers it was turned into a summer stock theater in the 1930’s. Many famous actors have walked on its stage including Katherine Hepburn, Marlon Brando, Helen Hayes and Betty Grable.
The building now houses two theater and produces year-round professional productions of musicals, comedies and dramas. It also has a number of summer productions for children.
4. James Pharmacy – Old Saybrook, CT
Originally called Lane’s Drugstore, it was operated by Peter C. Lane, one of two black pharmacists in Connecticut in 1895. Lane added an ice cream parlor and later brought in his sister-in-law, Anna Louise James, as a partner. She eventually took over in 1917 and renamed it the James Pharmacy.
Anna Louise graduated as the only woman in her class from Brooklyn College of Pharmacy in 1908 and became Connecticut’s first African American woman pharmacist-no small feat. She never married and ran the business until she retired in the 1960’s.
The building’s origin also has historical significance. Built in 1790, it was originally the general store for the Humphrey Pratt Tavern in Old Saybrook. Humphrey Pratt was the brother of Deacon Timothy Pratt, who built the house next door—that is now the Deacon Timothy Pratt Bed and Breakfast. Its claim to fame is that Lafayette (the famous French soldier) made a purchase there in 1824.
Today, it is a casual dining restaurant serving Moroccan food but it still has an ice cream counter and many of the original historic details from Miss James’s day. It also sells homemade chocolates.
5.Goodspeed Opera House, East Haddam, CT
The Goodspeed Opera House was built in 1876 by William Goodspeed who ran his shipping and banking business as well as a venue for theatre and opera. It passed hands and functions over the years until 1959, when Goodspeed Musicals restored the building, and the Goodspeed Opera House was reborn. Today it features musical productions year-round.
Join our Private FB Group for more travel inspiration and tips! JOIN HERE
You can also go behind the scenes of a musical during a tour of this gorgeous Victorian mansion and see backstage and the actors’ dressing rooms as a member of the Goodspeed Guild tells you about the vibrant history of the opera house.
Tours are on Saturdays from June-October from 11-1pm.
6. Connecticut River Museum, Essex, CT
Learn about American history during the War of 1812 when 136 British sailors rowed up the Connecticut River to Essex (then Pettipaug) to raid and burn privately owned warships. Called privateers, these ships were licensed by President James Madison to capture enemy vessels. The British burned 27 ships marking it as the largest single maritime loss of the War.
One of its other permanent collections features a virtual “art walk” over 410 miles of the River from New Hampshire to Long Island via amazing aerial photography in its Vertical Gallery.
But this museum is more than just art and historical exhibits, it has tours of the river by boat, canoe and sunset cruises.
Open Memorial Day-Labor Day, daily 10-5. Closed Mon. Sept-May
7. Essex Steam Train & Riverboat, Essex, CT
The 2.5 hour steam train and connecting riverboat excursion is the only one of its kind in the U.S. Starting at the historic 1892 station passengers board a vintage rail car that looks like something out of Harry Potter. The train travels along the River through the countryside and then visitors board the Becky Thatcher Riverboat at Deep River Landing for an hour long cruise on the river.
Nearby Historical Accommodations
Saybrookpoint Inn & Spa – 2 Bridge Street, Old Saybrook, CT
This inn has luxury accommodations, spa, and gourmet seafood restaurant located on the Old Saybrook Point marina. It also has an adults-only guesthouse, the Three Stories, created from a historical residential property but now completely renovated with rooms dedicated to local historic figures, including one that honors Anna Louise James.
Griswold Inn – 36 Main Street, Essex, CT
Described as one of the oldest continuously operated inns in the country, this historic pub and inn opened its doors in 1776 to patrons from sea and land.
Deacon Timothy Pratt Bed and Breakfast – 35 Main Street, Old Saybrook, CT
Step back in time in this circa 1746 historic colonial B & B. It has period-inspired rooms, some of which that still have their original wide plank floors and fireplaces.