This is probably the area in Connecticut that I am most familiar with considering it’s right in my backyard. I love our area this time of year it’s full of fantastic color and a plethora of things to do. I must admit I didn’t do this whole drive in one day because there are places that I go to all the time so I omitted them from my route.
Peak foliage time for this region is estimated to be from October 24th to November 14th.
The drive is estimated to be about 70 miles give or take. If you start out early in the day one day should be enough to enjoy a bulk of this region. I am going to leave out the city of New Haven in general; because I suggest a full day’s visit there. There is just too much to do because of Yale, the museums, shops and the green will take a full day on its own.

- You should begin in New Haven.
- Take I-95 north to exit 51.
- Pick up Route 1, then 146 east and continue towards Guilford.
- Turn north on Route 77 to Durham.
- Then turn north on to route 17.
- Head west on Routes 147, 157, and 68.
- Take 691 west towards Cheshire and get off exit 3. Then take a left to 10 south.
- Take Route 10 south to New Haven to close the loop.

Points of Interest:
Hubbard Park/Castle Craig is a must see in autumn. Anyone who grew up in Meriden which is affectionately called the “dirty den” knows that they have to take the annual pilgrimage up to Castle Craig to take in the breathtaking views. You can either hike up there or drive your car I brought Logan my 3-year-old hellion up with me and he loved it. It closes at 4:45 pm daily and is only open until October 31st. It reopens in the spring. Look out for special nights where they are open later to observe a full moon or the sunset.
The Quinnipiac River passes through many towns that have trails adjacent to it. Meriden has a lovely trail along with Wallingford, Cheshire, and Hamdan. I have personally been to the Meriden and Wallingford trails and both are very nice. They have a very wide path that allows you to bike along it if you’d like. The trails are open year round and are well maintained.
Another stop that I visited is Bishops Orchards. I will admit it was my first time going here since I’m a huge Lyman Orchards fan but this place definitely does not disappoint. They had a huge pumpkin patch where you could pick your own pumpkins along with being able to pick your own apples. What sets this place apart is the fact that they have their own vineyard there as well. I went inside and sampled many of the wines that they had to offer and they were quite good. (Tip: go on the weekend or else it will be a madhouse)
The Shore Line Trolley Museum is a fantastic place to visit. It took me about 2 1/2 hours to see everything and for me to take my trip aboard the trolley. Its claim to fame is that it’s the oldest continuously running suburban trolley line in the USA. The cost of admission is $10 but you can save a dollar if you are a AAA, Big Y card holder, or served in the military. The ride is short about 15 minutes but it takes you to the yard where you get a tour of the grounds and other cars they have on the lot. They offer a haunted trolley ride and a Santa ride as well that are worth checking out.
Something that I haven’t done yet, but it is on my bucket list of things to do is to take a Thimble Island cruise out of Branford to see the Thimble Islands. I could imagine that they are quite spectacular this time of year. The Sea Mist offers these tours and they are about 45 minutes. You can take a tour on Mondays, Wednesdays, Fridays, Saturdays, and Sundays in September and in October it runs only on Saturdays and Sundays. It is $13 dollars for the tour. **CASH ONLY** The tours run on a first come first serve basis and they do not accept reservations. (203) 488-9805 to call ahead for times.
