Five bike rides to check out around New Haven

In 2020, I was sharing with you four perfect spots to go kayaking in New Haven to be socially distant from people. But 4000+ of you read it, bought a kayak, and now I cannot get drunk on my kayak without seeing my neighbours, or that clingy friend I told I was busy and now it’s awkward for you to see me not being that busy, or my ex (there is a reason we are exes Michael, don’t come too close!).

Now all New Haven are now avid kayakers, and I need to find another sport to be alone with my many, Many, MANY…. thoughts. We are all pretending the pandemic is over, but I still would like to pretend it’s because of Covid I don’t want to be too close to you.

Time for another sport! How do you feel about biking?

1 – The Farmington Canal Heritage Trail: bike & snack!

Running 81.2 miles, the Farmington Canal Heritage Trail (FCHT) is a pedestrian/bike path going from New Haven to Northampton in MA. Not unlike someone going through a rough phase changing their hair colour every few weeks to find some sense of control, the FCHT is Connecticut’s version of hair. First a canal linking New Haven to Northampton in 1835 (remove all the dirt!!), it became a railroad in 1847 (actually, put back all the dirt and add steel), and finally a trail in 1996 (never-mind, remove the steel!). The last section to connect Hillhouse Avenue to Long Wharf was extremely delayed since the original plan was to dig a tunnel under the FBI building (Italian Job anyone?) but is it currently under construction and should be delivered in 2023.

It is the perfect trail to go for a bike ride, with multiple entrances and exit, you can choose how much you want to bike! Here are my two recommendation for the trial:

New Haven to Hamden

Starting point: 17 Hillhouse Avenue
Distance: 16 miles, way and back
Duration: 1hr 20 min
Points of interest: Shepard Brook, York Hill, MiKro
More info and full map:

Biking from New Haven to Sleeping Giant in Hamden is an awesome chunk of the trail, although the trail cross a lot of street exiting New Haven in Dixwell and Newhallville. Be careful at the crossings, the cars don’t always stop for bikers. On this section of the trail, you will bike by the marsh area of the Lake Whitney, you can refresh your feet in the Shepard Brook, and you can do a stop in the lovely forest backyard of a generous Hamden inhabitant who offers their property to the trail users.

And if you want a challenge, climb the hill at the 7.7 mile mark, all the way to the Quinnipiac University York Hill Campus! This one mile-long road has a 6% grade slope that will make you sweat, but the view on Sleeping Giant at the top is worth it, almost as much as the way down, flying like the wind!

As a reward, the brewery MiKro Depot, directly off the trail in the former train station is a perfect pit stop for a snack or a drink before heading back to The Have.

Make it a loop! Continue towards Sleeping Giant on Mt Carmet Avenue and come back to New Haven by Ridge Road (you will see amazing houses!) that will lead you all the way back to East Rock. The loop adds about 5 miles to this ride. Watch out, someone throw their full smoothy at me from a moving car on Ridge Road. It hit my leg and splashed the elderly man walking on the pavement next to me. I was mad at them at first but then I realized it was a kale smoothy so I understood. I would have probably throw it away too if I realized that high school kid at the juice bar added kale to my bro-smoothy…

Hamden to Cheshire

Starting point: Sleeping Giant
Distance: 14 miles, way and back
Duration: 1 hr 30 min
Points of interest: Lock 12, Wentworth ice cream shop
More info and full map:

Alternatively, if you want to avoid the road crossings, I recommend parking at Sleeping Giant and biking all the way to Cheshire on the trail. This is the quietest part of the trail (it gets busy with 250,000 users per year!) and you can stop to see the Lock 12 Historical Park, the last visible part of the canal on the way there, and stop at Wentworth for some well deserved homemade ice cream on the way back!

2 – The wealth and privilege bike lane

My editor censured my thin blue line joke…. This is what republicans must feel like when CNN won’t air their problematic thoughts.
Starting point: 1 Prospect Street
Distance: $42B, one way
Duration: 2 min
Point of interest: realizing you are poor
More info:

We know Yale is rich, but did you bike it?

On Prospect street by Grove Cemetery, you can see how much Yale is paying in taxes (in red) and you can bike up toward Science Hill until you find the end of Yale Endowment (in blue)! Yale students, community advocates and Yale union members painted this in May 2021 as a message to the university in front of President Salovey’s current office “Yale: Respect New Haven”.

This month marks the 8-year anniversary of me moving to New Haven, and since I arrived, Yale endowment doubled. I don’t want to take full credit for it, but you’re welcome!

3 – Florida to Maine: the East Coast Greenway

You find the 81.2 miles of the FCHT a little too short? Fear not, the East Coast Greenway got you covered! Connecting 15 states and 450 cities and towns for 3,000 miles, this bike route can bring you from Maine to Florida!

Follow the little tree signs (the trail/roads are well marked!) and you will enjoy a delightful bike ride .

New Haven to Stratford

Starting point: Long Wharf
Distance: 20 miles, one way
Duration: 2 hrs
Points of interest: Long Wharf Nature Preserve, West Haven Boardwalk, 
Silver Sand State Park, the beach houses on the ocean front in Milford
More info and full map:

I recommend starting on Long Wharf in New Haven where the bike path leads you through the Nature Preserve behind the highway to bring you to the West Haven boardwalk, the numerous beaches of Milford, the state park of Silver Sands with a view of Charles island. Perfect end of summer bike ride, pack a swimsuit and a towel and make numerous refreshing stops on the beach or grab a drink at Dockside Brewery by the Housatonic river.

As soon as you cross the Washington Bridge in Stratford, the pleasant beach towns where you biked turn into a highway nightmare and I would advice to just turn around before the bridge to go back, or catch a ride back with the Metro North at the Stratford train station.

4 – I don’t care where we go as long as it’s a party: the New Haven Bike Parties!

Distance: About 10 miles loops, multiples stops
Duration: Around 1h30
Meeting point and theme:

Every second Friday night of the month, it’s party time! New Haven Bike Party time!

Starting at different points and going through different routes each month, Bike Party is first and foremost a PARTY! There is music, and costumes and all kinds of celebrating (mostly yelling “BIKE PARTY” at every soul you cross)! Riders dress up (there is a different theme each month) and pimp their rides with lights, flags, and other elaborate decorations. The goal is to engage with the biking and local community, and discover neighborhoods you might not have been to before.

5 – Around East Rock Park: the Pardee Rose Garden

Starting point: Orange St
Distance: 5 miles, loop
Duration: 40 min
Point of interests: Rice field, Pardee Rose Gardens and its
glass greenhouses, many deers!
More info: Rose Garden

Tired of hiking up East Rock? Yeah me too! What about a loop around it?

Turn right at the Orange St bridge and pass the baseball field and continue around the park on State St (heavy car traffic here!). Turn left onto Park Road and you will get to see the impressive glass greenhouses of the Pardee Rose Gardens (if you use headphones for your ride, here is the perfect soundtrack). Spanning 2 acres, the garden features an array of flowers from early spring until mid fall.  Outside of these dates, it’s a barren wasteland, but it’s the other side of East Rock, what did you expect? We should just go through with the annexing plan…

Continue to the back entrance of the park and start your climb. After the second turn in the climb, turn left at the closed road (watch out for the chain!) and enjoy a gentle ride down the tortious road all the way back to the Rice Field. Don’t go too fast on the road, there is a lot of hikers, especially by the stairs, and many deers. Bike vs Deer, the odds are not good for your front wheel!

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