Our Story

Our Story


Our Story

Our Story


Welcome to Lakeside Watersports!

Started by two local guys who decided to share their passion for watersports with Connecticut’s greater Candlewood Lake region, Lakeside is based on two very important principles: Safety and Affordability.

It is our mission to provide every customer with fun-filled summer memories.  Come take a ride behind our boat and experience what it feels like to glide across the water with nothing but a smile on your face!

Lakeside Priorities


Safety is our number one priority.  Boating and watersports require quite a bit of preparation and responsibility. It is our goal to not only provide you with the best possible experience on the water, but also ensure the safety of everyone on board. All customers will receive proper instructions and top notch, Coast-Guard approved safety equipment. Rest easy know that your instructors have 1,000s of hours of boating and teaching experience combined with lifeguard and EMT training.


Our other main focus is promoting affordable watersports. We understand that enjoying the water can become expensive very quickly. The boat alone can be a huge expense, which does not even include the cost of gas and equipment. These prices will scare just about anyone away from the watersports lifestyle. Here at Lakeside Watersports, we intend to provide all kinds of summer fun, without having to break the bank.

Meet the Owners


The Teacher

Mike grew up on Candlewood Lake and has been riding in boats ever since he was a baby. He started to wakeboard while in middle school and has not looked back since! After teaching friends and family on Candlewood Lake, he began working at a summer camp in Maine teaching kids how to wakeboard and waterski. Mike worked his way up to the Program Director position for the entire Ski program, where he was in charge of a 14 person staff, two boats and two jet skis. At this camp Mike perfected his teaching method and has been very successful at getting just about anybody up and riding. Not only has Mike worked at a summer camp in Maine, but he has also worked for a watersports company in Orlando, Florida. While in Orlando, Mike came up with the idea for Lakeside Watersports. He realized the need for a watersports service provider in the northeast, and his history with Candlewood made it a perfect spot to make this idea a reality. As a graduate from the University of Connecticut with a Masters degree in Education, his career as a High School Social Studies Teacher allows him to not only teach kids in the classroom, but to also teach people out on the water during the summer months. Mike’s ultimate goal is to help others succeed both in the classroom and behind the boat. 


The Business Guy

Chris has the privilege of not only being good friends with Mike, but he is also one of Mike’s very first wakeboard students. Mike introduced him to the watersports culture more than ten years ago, and ever since then he hasn’t been able to get enough of it. Early morning sessions on Candlewood have become part of his summer routine.

After becoming proficient in wakeboarding, Chris began sharing his passion with friends and family, which proved to be a truly rewarding experience. As you can see, he is the business end of this partnership. Chris graduated from the University of Connecticut with a degree in Business Management: Entrepreneurship. A former lifeguard and swim instructor, while in college he moved into the corporate world, where he gained valuable business skills.  His schooling and professional experiences have given Chris the ability to organize the business operations of Lakeside Watersports LLC. Chris is excited about bringing watersports to Candlewood Lake in Connecticut. He has a true passion for helping people and having fun…Two things that Lakeside excels at!


Candlewood Lake

Candlewood Lake

Candlewood Lake

Candlewood Lake

Believe it or not, Candlewood Lake’s majestic beauty is man-made. In the early 1900s, the Rocky River Valley was a farming community at the foot of the Berkshire Mountains.

During the summer of 1926 the decision was made by Connecticut Light & Power to create a lake in this region that would generate hydro-electric power.

After the power company relocated all of the valley’s residents, a 100 foot-tall dam was constructed at the northern end and water from the Housatonic was pumped into the valley. The project took nearly two years. Well worth it to create our beloved Candlewood.

Candlewood Lake Sunset Circa 2016

Candlewood Lake Sunset Circa 2016

Facts about Candlewood Lake

Connecticut’s Largest Lake

Maximum Length: 11 miles

Maximum Width: 2 miles

Deepest Point: 90 feet

Average Depth: Approx. 30 feet

Shoreline: Approx. 65 miles

Lake: 5,420 acres or 8.4 square miles

Islands: 12 total

5 Bordering Towns: Danbury, Brookfield, New Milford, Sherman, & New Fairfield

Lake Divides: Fairfield & Litchfield Counties

Main Water Source: Housatonic River

Man Made: Started July 1926 – Completed February 1928

Generates: Hydro-Electric Power

Fishing Hot Spot: Trout and Large and Small Mouth Bass


Lake Winnipesaukee

Lake Winnnipesaukee

Lake Winnipesaukee

Lake Winnnipesaukee

Facts about Lake Winnipesaukee

New Hampshire’s Largest Lake

Maximum Length: 21 miles

Maximum Width: 9 miles

Deepest Point: 187 feet

Average Depth: 43 feet

Altitude: 504 ft above sea level

Shoreline: Approx. 288 miles

Lake: 71 square miles

Islands: 258

Bordering Towns: Alton, Gilford, Laconia, Meredith, Center Harbor, Moultonborough, Tuftonboro, Wolfboro

Source: Glacial Lake

Main Inflows: Gunstock River, Merrymeeting River, Melvin River, Red Hill River

Main Outflows: Winnipesaukee River

Vintage Summer Resort: People have been visiting Lake Winnipesaukee as a summer destination for well over a century.

Winter Fun: Gilford is home to Gunstock Mountain, a popular winter ski resort. Hit the slopes before the summer season kicks off.

The Native American name Winnipesaukee has two meanings, “Smile of the Great Spirit,” or “Beautiful Water in a High Place.” We are just fine with either of these descriptions.

Lake Winnipesaukee is an incredibly beautiful destination with views of Mt. Washington in the distance and crystal clear water that you can see the bottom up to about 15 feet. This destination defines what lake living in New England is like.

Not only is it beautiful, it is huge! As New Hampshire’s largest lake, it actually ranks as the third largest in all of New England, just behind Lake Champlain in Vermont and Moosehead Lake in Maine.

Winnipesaukee Pier Circa December 2018. Future home base of Lakeside Watersports.

Winnipesaukee Pier Circa December 2018. Future home base of Lakeside Watersports.


Frequently Asked Questions


Frequently Asked Questions



Frequently Asked Questions

If you have been out with us before, you know that we spend almost all day on the boat teaching wakeboarding and waterskiing; basically just having a great time on the water. This makes it hard for us to find the time to answer the phone when you call. Here are the answers to many of the common questions we get.

If there is a question we haven’t answered here, give us a call. Leave a message. If we don’t answer at first, we promise to call you back by end of day.



No, we do not rent jet skis. Although jet skis are fun to buzz around the lake on, there are laws that prevent operating a jet ski without a proper Personal Watercraft/Safe Boating Certificate. For this reason, we are not able to rent jet skis. Please check local and state laws to confirm where you might be able to rent a jet ski.


HOW MANY People Fit on the Boat?

12 is the maximum number of guests that we can take on any of our boats at one time. This leaves room for the driver and the spotter to operate the boat safely and legally. If you have a group size larger than 12 total, please call us. We are happy to offer creative solutions to make sure everyone in your group can find a way to enjoy the Lake.



We charge a flat rate of $180/hour. Again, this is a flat rate, meaning we charge by the hour. This is NOT a per person charge. If you have a large group, the price per hour remains the same at $180/hour.

This includes the boat time, driver, spotter/instructor, gas, watersports equipment, and safety gear.

should i tip the crew?

The Lakeside staff strives to offer the absolute best time on the water while keeping you safe. It’s customary to offer gratuity, but never required. Gratuity can be added during checkout with a credit card or cash can be handed directly to the crew.



We are incredibly accommodating and are willing to let you and your guests try whatever watersports you would like during your appointment time. Just tell us what activities you’re interested in before we leave the dock, and we will be sure to stock the boat with all the necessary equipment. The cost remains the same per hour regardless of how many activities you try.



We leave this decision up to you, but we can help make recommendations. A good rule of thumb for making a booking for a beginner is 20-30 minutes per person per activity. Watersports like wakeboarding and waterskiing are incredibly tiring. 30 minutes per person gives enough time for someone to try without being completely exhausted. It might also leave some extra time for tubing.

Note: We will do our best to manage the time you book and give everyone a chance who wants one. But be advised there are scenarios where too many guests and not enough time booked make that harder to accomplish.



We prefer if you show up 5-10 minutes before your start time. This gives us time to get your waivers filled out, life jackets fitted, and equipment loaded onto the boat for an on-time departure. We book our appointments back-to-back, so there is a possibility that if you show up very early we will not be at the shop and will be out on the water with another group.

If you want to save time on the day of your appointment, each person going on the boat needs to fill out the waiver. If you plan to come back this season, this needs to be filled out once per year per person.



Yes! Just as the Lakeside Watersports name suggests, we make lakeside pickups. If you would like to be picked up, you need to specifically tell us that before your appointment. We assume that all appointments will start at our office location unless otherwise instructed. If you want to be picked up, tell us the street address, any helpful landmarks to look for, and what equipment we need to bring.

Connecticut: We can pick you up anywhere on the lake, so long as there is a safe docking location.

New Hampshire: Due to the size of Lake Winnipesaukee, we can only offer lakeside pickup in Gilford, Laconia and Meredith. If you live/are staying outside of these towns, we apologize but you will need to travel to our location at the Winnipesaukee Pier or book more time to compensate for our extended travel time.

Note: Requesting a lakeside pickup has the potential to delay the start time of your appointment by a few minutes while we travel to your location. We will do everything we can to get to your location by the requested start time, but we ask that you be patient based on lake and weather conditions.


Customer Reviews

Customer Reviews

Customer Reviews

Customer Reviews


Our reviews are collected and verified by Genbook.

We invite you to read what our happy clients have to say about Lakeside. Here is a sneak peek.



"We had never been to Candlewood Lake before and these guys showed us a great time. They were knowledgeable, professional, encouraging, and made sure we all had fun. Slick boat, top notch gear. Can’t wait to do it again!"



"We had a great time and hope to return this summer. These guys were very helpful and we definitely recommend this place. Lots of different activities to try between wakeboarding, tubing, etc."



"I surprised my husband with with an afternoon of waterskiing lessons for his birthday. We took our two boys and they learned too. I loved seeing the smiles on all of their faces. We now have a new family activity that everyone enjoys!"

-Michele L.


"We had a great time at Lakeside!! With the help of Lakeside my friend and I learned to wakeboard and got up on our first try! The boat was also so comfortable and clean!!! Had a great time can’t wait to go back!!!"



"Had a great time. My only regret is not booking more time… Boat was comfortable and all equipment was clean and in excellent condition."

-Mike B.


"I could not have asked for more, these guys were great! They had me popping out of the water, and wake surfing within 15 minutes! They offered excellent instruction throughout the entire session which made it easy to pick up."

-Todd W.






New Season. Bigger Boat!

In 2019, Lakeside Watersports will be powered by East Coast Flightcraft.

For Candlewood Lake, they have helped us secure a bigger boat that can handle larger group sizes. We used to drive Axis A20s and now we will have a brand new Axis A22. The additional 2 feet mean that the maximum size group we will be able to take is now up to 12 guests. Be the first on the schedule to get a ride in this new boat and invite your friends to join!


Interested in testing out a new Axis or Malibu boat? Schedule a demo with:

Or book an appointment with us!

2019 AXIS A22

Single Propeller Inboard Design

Surf Gate Equipped w/ Power Wedge III

Length: 21’ 11” (Excluding swim platform)

Beam: 102″ (The width of the boat)

Draft: 27” (Amount of boat that sits in the water)

Seating Capacity: 12 guests or 2,041 lbs

Dry Weight: 4,500 lbs

Max Ballast: 4,115 lbs.

Engine: Monsoon 410 HP 6L V8

Hull Type: Wake Plus



Our Partners


Our Partners

We get by with a little help from our friends