Whether you’re a beginner or an expert paddler, Pleasant Bay on Cape Cod offers something for everyone. In this post, we’ll explore three fun kayak trips launching from Jackknife Beach in Chatham, each catering to different skill levels. Let’s dive in!

Launch Point: Jackknife Cove in Chatham

Jackknife Beach is located on the Jackknife Cove portion of Pleasant Bay, right off of Route 28 on the Chatham/Harwich line. We chose Jackknife Beach as a starting point for a few reasons:

• Free beach access and parking (a rarity on Cape Cod!)
• Jackknife Beach in Chatham allows dogs all summer long (another rarity!)
• Different water conditions to match all skill levels

Free Parking at Jackknife Cove

When parking here be aware that at high tides during certain moon cycles the water can flood portions of the parking lot. The further you drive into the lot the more sandy it becomes. 2wd vehicles should be careful about driving in too far, the last dozen spaces are in soft sand. And be very careful pulling in and out on Route 28, it can get crazy.

Note that you can park along Route 28 on the Harwich side without a parking sticker too. But it’s a bit dicey unloading a kayak with cars screaming by so you’ll find it a lot easier in the Chatham lot. Dogs aren’t allowed on the Harwich side during the summer season, so stick to the Chatham lot if you have your pet with you.

Trip 1: Lazy Paddle Up Muddy Creek (beginner)

Distance: Approximately 2.4 miles round trip
Skill Level: Beginner
Shark Risk: Very low

Kayak Route Details

Launch your kayak from Jackknife Beach. Paddle to the left under the route 28 bridge into Muddy Creek. The calm waters make this a perfect trip for those just starting out.

At low tide you’ll need to follow the deeper part of the river as you make your way to the bridge, it can get very shallow. For the easiest possible paddle try to time your trip so you’re padding under the bridge as the tide is coming in, and paddling back as the tide starts going out.

Paddling under the bridge against the current takes a lot of effort, so plan accordingly around the tides. We’ve definitely been stranded for a bit on days with high currents when using an inflatable stand up paddle board, but it was less of an issue in kayaks.

The current will move the fastest 3 hours after the day’s posted high or low tides. It’s much easier to paddle at slack tide, which occurs at the posted high or low tide time, when the current stops moving and changes direction.

If you do get stuck and can’t cross under, remember that the large rocks on the sides under the bridge are slippery and sharp, tough to navigate when pulling a kayak. Worse case when people are stuck they sometimes wade into the river while dragging their kayak. But better to just time the tides and avoid the hassle altogether.

Weather conditions aren’t a huge factor here in the creek since it’s fairly well protected from wind. There’s no boats in this area so there’s no motorized obstacles to avoid, just the occasional log. Keep an eye out for blue herons and other cool wildlife.

Nugget loves this trip, it’s a great low energy float for dogs! It’s a very relaxing paddle. It’s a great place to teach your dog how to ride in a kayak or stand up paddle board off of the main beach. Once they get the hang of it you can navigate into the creek and begin.

Trip 2: Day Trip to Sipson Island (intermediate)

Distance: Approximately 4.5–5 miles round trip
Skill Level: Intermediate
Shark Risk: Low

Sipson Island is a great day trip by kayak. It has 24 acres of sandy beach, coastal banks, saltmarsh, eelgrass beds, upland meadows, and woodland. The island was bought by English colonists in 1711 and remained in private hands until recently when it was opened to the public. Learn more at the Sipson Island Trust website.

The paddle here is much longer and the water will be choppier than in Muddy Creek. The wind can really pick up across the open water, so make sure to use a dry bag and expect to get a little damp — nice on a hot day!

From shore at Jackknife you can see the island off of the far left coastline, to the right as you stare out. It looks attached until you get closer and then you’ll see the channel separating it from the mainland. Use the height of the trees in the distance to gauge how far away you are as you approach, it can be a bit deceiving.

Kayak Route Details

Paddling to Sipson Island is a great day trip across Jackknife Cove on kayak. There are three ways you could reach it from the launch point off of the beach.

• Paddle along the coastline to the left (2.6 miles each way): As you look at the water from the launch site, passing the Wequassett Inn. You’ll continue along until you reach a thin channel and reach the island. This route has you paddling within distance of shore for the entire journey, much safer in case you run into issues. It’s not a hard paddle, but can be a lot for novices or children.
• Paddle coastline to the right (2.4 miles each way): Pass by the golf course to the end of the mainland, and then cut 1 mile across the harbor past to Sipson Island. You’ll have a bit more open ocean to cross here, but the conditions are usually relatively easy.
• Paddle directly to the island (2.2 miles each way):, cutting right across Jackknife Harbor in a straight line. Watch out for boats and be careful on days with limited visibility. This route is a little shorter and adds to the adventure when you see a seal pop up nearby and start wondering if there’s a great white shark as well.

Simpson Island is a public area accessible only by boats. Nugget didn’t really enjoy this trip when we took her. Dogs aren’t allowed on the island unfortunately. The wind kicked up water for much of our return journey, and she didn’t find that very fun at all.

If you don’t have a dog then plan to stay for a picnic. The beaches near the channel grow wider at low tide and are a great place to pull up your kayak.

There’s a small dock that’s located in really shallow water but perfect for kayaks. It is located on the northwest side of the island, just beyond the beach at the point of the channel.

Your risk of meeting a shark on this trip is low. But we saw a few seals out by Great Island and in the channel. As with any ocean beach on cape cod there’s a risk. By staying close to shore and crossing the channel you definitely minimize your exposure compared to taking a straight line right across the bay..

Trip 3: Paddle to Nauset Beach Across Pleasant Bay (expert)

Distance: Approximately 6 miles round trip
Skill Level: Expert
Shark Risk: Medium

Nauset Beach is one of the coolest beaches in the world. The backside of the beach stretches down forming the eastern edge of Pleasant Bay. It’s a challenging full-day kayak trip that is one of the most rewarding paddling adventures on Cape Cod. You can enjoy the soft sand beaches of the bay, or walk across to the miles of rugged shoreline facing the open Atlantic.

Be advised this route crosses a very large open waterway and is for expert kayakers only. Do not attempt this trip unless you really know what you’re doing.

Shark safety matters here. The ocean-facing side of Nauset is one of the biggest great white hotspots in the world. Sharks are typically not seen within Pleasant Bay where you’ll be kayaking. But seals are there. And sharks can easily cruise within the cut on the south side of Nauset and enter the bay waters. People kayak on the outer cape beaches all the time, but that doesn’t mean it’s entirely safe.

Make sure the weather conditions are good. Clear visibility, not too hot or windy, etc. Minimal surf conditions are a must. Time the start of your journey to occur with the outgoing tide, and return as the tide comes in for easier paddling. Watch for the wind direction, and remember paddling back into the wind will be a real workout.

Nauset Beach is an awesome place to hang out all day. Killer sunrises over the open ocean, and killer sunsets over the bay. But if you’re kayaking you’ll need to forego the sunset to make sure to allow for enough time to return in the daylight, and pad your timing for safety. Especially if you have to paddle into the wind or against the tide.

On your journey out for a slightly longer trip head diagonally up to Sipson Island, stopping by to rest. From there you’ll be more than halfway there across Pleasant Bay. Crossing through Little Pleasant Bay means you’ll run by some boats, so be aware.

If you want to head around Great Island there’s a marsh to explore. You’ll want to stay far north of the cut connecting the bay to the open sea on the south side of North Beach. The strong currents there are a safety liability. Please do not paddle out foolishly and get sucked out to sea Into great white shark territory. You were warned!

Nauset Beach allows pets for most of the year, but the ORV trails are typically closed due to nesting piping plovers and dogs are restricted during that time. Taking a dog on this trip is generally a poor idea anyway, it’s far too long a journey unless your dog is a real hearty adventurer.

How to Time Your Kayak Trip with the Tides

When planning your trip, try to have the return trip occur when you’re traveling with the tides. For Muddy Creek, return when the tide is going out. If you’re venturing out into Pleasant Bay to Sipson Island, Nauset, or beyond, plan to travel back with the incoming tide.

Remember the 50/90 rule for kayaking: the tide moves at about 50% speed one hour after high tide, 90% after hour two, 100% at hour three, then it backs down to 90% at hour four, 50% at hour five, then slack tide occurs at the changeover to low tide at hour six. If you must paddle against the tide, it’s always strongest 3 hours after the posted high or low.

Conclusion

Pleasant Bay offers fantastic kayaking trips for all skill levels, and Jackknife Cove is a convenient place to launch. Remember to respect the environment, follow safety guidelines and have fun!

Happy paddling!

Other Fun Kayaking Adventures on Cape Cod

• Big list of the best places to kayak on Cape Cod
• Guide to kayaking the BassRiver
• Kayaking at Nickerson State Park

If you’re looking for a fun day of kayaking on Cape Cod, the Bass River is a great place to start. Located between Dennis and Yarmouth on the southern side of the cape, this tidal estuary is the perfect place for beginners as well as for experienced paddlers looking for a challenging trip.

For a full list of other fun paddling adventures on the cape, check out:

• A big list of the best places to kayak on cape cod
• Our guide to kayaking at Nickerson State Park

Bass River Launch Points and Routes

Now that you’re all set, let’s explore where to launch your kayak on the Bass River and the best routes to take.

Popular Launch Sites

• Bass River Beach and Boat Access in Yarmouth ($)
• Uncle Freeman’s Road in West Dennis
• Ferry Street Landing
• Bass River Park
• Horsefoot Cove Landing
• Aunt Julia Ann’s Landing
• Cove Road North Landing
• Old Main Landing (in Grand Cove)
• Cove Landing South
• Highbank Road Landing (Wilbur Park Launch)

Many of the parking options above are free. There’s a daily charge at the Bass River Beach lot, and you have to paddle out at a busy double boat ramp, so this isn’t recommended for beginners or people with families. However, a quick paddle across the river lands you at the back side of Bass River Beach aka Smuggler’s Beach, which is one of the nicest places to pull off on the entire river.

Much calmer launch options can be found at Bass River Park, Uncle Freeman’s Road, and Wilbur Park. Free parking there too, which is a plus.

Beginner-Friendly Routes

For those new to kayaking, we recommend starting with these gentle routes:

• Route 1: Bass River Park under the Route 28 Bridge: A short, scenic paddle perfect for beginners. Plan to paddle into the tide going out so that you can have an easier paddle back. When the tide is out there are a lot of exposed sandbars and shallow areas to hop out of your kayak just across from the launch point. Great place to park for a while and let your dog hop out.
• Route 2: Wilbur Park north to Kelley’s Bay: Enjoy the calm waters and beautiful views on this leisurely paddle. Located on the northern side of the Bass River, beginners can stick to the sides to avoid boat traffic and passing water skiers. Wilbur Park has a small sandy beach which makes it easy to launch from. It’s not as nice a beach as further south at West Dennis Beach, but it’s the perfect launch point to go north into Kelley’s Bay and beyond into Follins Pond.
• Route 3: Bass River Park to Wilbur Park: Plan around the tides to determine which location to start from for the easiest paddle. If the tide is coming in, it will be easier to paddle upriver to Wilbur Park. If it’s going out, the downriver paddle to Bass River Park will be easiest. Both locations have ample free parking and a calm, open area to launch from so they’re great places for families or if you’re taking your dog on their first kayaking trip.

More Challenging Kayak Day Trips

If you’re looking for a full-day kayaking adventure, the Bass River provides! Full-length trips starting at the mouth of the river begin at the Bass River Beach and Boat lot in Yarmouth. It’s best to check the tides and wind conditions when planning your route.

If you’re looking to paddle upriver and back, Ideally you’ll paddle with the tides in each direction and if the weather cooperates you’d have the wind at your back for the ride back which makes for an easier, drier paddle home. If you’re planning a 6 hour roundtrip, try to begin paddling 3 hours before high tide, so that halfway through you reach slack tide, and then have the tide going out for the 3 hours of your return trip.

If you only want to travel one way, you can park a car at the mouth of the river and launch from a second vehicle further upriver. This is helpful if you’re looking for a lower-energy booze cruise and plan to stop off for extended rests on the beaches you pass.

• Follins Pond to Bass River Beach: This route will take you on a paddle through the entirety of the Bass River. The Follins Pond boat launch is located at the northern side of the river. It’s not ideal to launch boats due to the state of the boat ramp, so it gets less use than it used too, making Follins Pond a great spot to launch a kayak.
  
  You’ll pass a few beaches and picnic spots along your way. Stop off for a bite mid-trip at Sundancer’s or the Summer Shanty as you rest up. You’ll end the trip by passing the backside of West Dennis Beach on your left, then exiting into Nantucket Sound and taking a right so you can land on Bass River Beach. Beware of conditions on the open ocean and watch out for boats in the channel.
  
  If you’re able to park a second car at the other end and do a one-way trip, plan to ride the outgoing tide and with the wind for the easiest, driest paddle. If the tide is coming in on the day of your trip, start at the mouth of the river and work your way up.

Public Beaches on the Bass River

While much of the shoreline is developed by rich people who don’t want you on their private beaches, there are several public beaches to stop off at on your kayaking trip.

• The best public beach on the Bass River is the backside of West Dennis Beach. Popular with boats and kayaks, located just across the river near the Bass River Boat Launch in Yarmouth.
• Paddling out of the Bass River into the open ocean also gives you quick access to the lengthy shores of West Dennis Beach to the left, and Bass River Beach on the right. Keep in mind these beaches don’t allow dogs in the summer season.
• Wilbur Park has a public beach that does allow pets. It’s a great place to picnic. Good choice to launch for families who just want to let kids float around a bit
• While not truly a beach, the tidal flats at low tide across the launch from Bass River Park are a perfect place to hop out and anchor a kayak.
• Another small beach is accessible below the cliffs of the golf course as the tide recedes, on the left side as you head upriver.

Bars and Restaurants on the Bass River

There’s a few options if you want to grab food and drinks on your kayaking trip. If you have your dog with you, you’ll need to get your food to go.

• Sundancer’s: Just north of the Bass River Park launch sits the access point for Sundancer’s. There’s a long dock area for boats, and kayaks can pull up off the beach. By day it’s a riverside seafood eatery, by night it’s a club where people have been partying for decades. We don’t recommend getting drunk and paddling home at night though.

• Summer Shanty: The Summer Shanty is located just north of Sundancer’s at the Bass River Marina. Just be careful when crossing the thin channel leading to the Marina, boat traffic is often very heavy here. They have a seasonal outdoor patio and sometimes there is live music.

Dog-Friendly Kayaking Tips

Kayaking is even more fun with your dog! Here’s how to ensure they enjoy the adventure too.

If your dog hasn’t kayaked before, Introduce your dog to the kayak on dry land first. Use treats and positive reinforcement to make them feel comfortable. Equip them with a doggy life jacket for safety.

Safety Considerations
Keep your dog hydrated, and provide them with a comfortable spot to sit or lie down in the kayak. Shade is important on hot days, especially with older dogs. Always keep an eye on their well-being.

Make sure to use a dog life jacket, even if your dog is a good swimmer. Be careful letting your dogs swim in areas with boat traffic, or on days with limited visibility.

Preparing for Your Kayaking Adventure

Before hitting the water at the Bass River, let’s make sure you’re fully prepared for a safe and enjoyable kayaking trip.

How to Plan Your Kayaking Trip Around Tides

Whenever you’re kayaking in a tidal estuary like the Bass River, it’s important to pay attention to the tides. Check Bass River Tide Chart

Try to paddle your return trip so you’re going with the tide. The current will move the fastest 3 hours after the day’s posted high or low tides. Slack tide occurs when the current stops moving and changes direction.

What is the 50/90 rule for kayaking? The 50/90 rule states that the tide moves at about 50% speed the hour after high tide, 90% after hour two, 100% at hour three, then it backs down to 90% at hour four, 50% at hour 5, then slack tide occurs at the changeover to low tide at hour 6.

Keeping the tides in mind while planning your kayaking trip can save you a lot of effort and allow you to explore longer trips with the same amount of effort.

Choosing the Right Kayak

For beginners, a stable and comfortable kayak is key. Look for recreational kayaks designed for calm waters. They’re easy to maneuver and offer a great balance between stability and speed.

The wave conditions most days are small enough to be suitable for sit-inside kayaks. Windy days you can expect to kick up some spray paddling into the wind. Be careful by the mouth of the river or when passing boat wakes approach.

Sit-on-top kayaks work well too, but you should plan to get a little wet. Keeping scupper plugs inserted can elevate you out of the water a bit more, but also make you more susceptible to wind.

Essential Gear

Don’t forget these must-have items:

• Life jacket (for you and your dog)
• Paddle
• Dry bags for your belongings
• Sun protection (hat, sunglasses, sunscreen)
• Plenty of water and snacks

Safety Tips

Safety first! Always wear your life jacket, check the weather forecast, and be aware of your surroundings. Avoid days with limited visibility or potential storms. A quick review of basic water safety can go a long way in ensuring a smooth trip.

The Bass River can get very busy with boat traffic. Be aware of channel markers and cross channels perpendicularly to minimize risk of passing boats.

After Your Kayaking Adventure

You did it! Here’s what to do next.

Post-Kayaking Care
Rinse off your kayak and gear with fresh water to remove any salt or dirt. Stretch and relax to ease any muscle tension. Crack a cold drink and relax – you earned it!

Time to chow down
Hungry? Check out our listings for dog-friendly restaurants on cape cod.

Find a beach and relax
If you wrap up early then find a beach! Check out our dog-friendly beaches page to find options nearby in Dennis and Yarmouth, and throughout Cape Cod.

Note: during the summer season, most public beaches near the Bass River don’t allow dogs, but if you’re willing to drive a little then your options increase. Consider one of the Cape Cod National Seashore Beaches for your best pet-friendly options.

Conclusion

Kayaking on the Bass River is a delightful experience for beginners and their dogs. The calm waters, beautiful scenery, and abundant wildlife make it an ideal spot for a day of adventure. So grab your kayak, gear up, and explore the Bass River—you and your furry friend are in for a treat!

Other Fun Kayaking Adventures on Cape Cod

• Kayaking at the ponds of Nickerson State Park
• Guide to kayaking the Bass River
• 3 Kayak Trips in Pleasant Bay for all skill levels