Oak Island Backpacking Loop– Backpacked from dock to the Northwest Beach, out to the overlook and then on to North Bay campsite #6. From North Bay we hiked down to the Sandspit via the Loop Trail before finishing on the sandspit trail returning to the dock.
Distance- Approx. 15.7 mile loop plus the inevitable beach walks you may complete. Short day hikes from the dock include 3.0 miles roundtrip from the Dock to the Sandspit or roundtrip to the Northwest Beach is 4.1 miles. A longer daytrip option would be 7.0 miles to the overlook and back.
Difficulty- Moderate (as far as backpacking routes go)
Description- The Oak Island loop takes in lonely beaches, oak savannah, a dramatic Apostle Islands overlook and a 4 mile section through the inland portion of the island. Nightime provides ideal conditions for star gazing (VERY dark skies at a couple of the sites) and possible Northern lights viewing from campsites #4 and #6.
Elevation Maximum: 1081 feet
Elevation Minimum: 600 feet
DIRECTIONS:
Take WI Hwy 13 north to Ashland or Hwy 2 to Ashland and then follow Hwy 13 North to the small town of Bayfield, WI. The dock is right along the waterfront at downtown Bayfield. (See map).
NOTE: Although this is written in the form of a 15.7 mile backpack route you can easily camp at the dock and do shorter hikes to the sandspit, overlook or other sights.
Dock-Northwest Beach (4.1 miles Roundtrip)
Oak Island, one of the most accessible islands in the Apostle archipelago, makes for a great introduction to backpacking and to the Apostles themselves. If you haven’t done a lot of backpacking but wish to give it a try, make sure to look into a visit to one of the more visited Apostles, Oak Island. Keep in mind that it’s not the easiest place to reach under your own power. Oak Island requires you to either have access to a sea kayak, Great Lakes ready boat or a ferry ride that ain’t exactly cheap. If you can just reach the island you will find that it is oh so worth it though!
By way of introduction, the Apostle Islands National Lakeshore consists of 20 islands and 1 “almost island” which became connected to the mainland sometime in the 1970’s (Long Island) and a strip of land on the northern end of the Bayfield Peninsula known as the mainland unit. Madeline Island, the most visited island in the whole archipelago, is actually not part of the designated National Lakeshore.
The Apostle Islands may be some of the most spectacular real estate in all of the Midwest. I would consider them to be at the very least one of the 7 natural wonders of the Midwest. This set of islands are a truly amazing playground for anyone with a sea kayak but make sure you’re well acquainted with paddling “big water”. This can be an unforgiving place for beginning paddlers but as I mentioned before you can still make a beginners backpacking trip to this beautiful region. Thankfully, there are water taxi services and the Apostle Islands cruise services to shuttle you out to the islands even if you don’t have your own boat.
My eldest daughter and I made the voyage out to Oak Island with the intention of looping the island on it’s 8 mile path that makes a complete circle. The mileage on our route would actually total a much higher tally due to the off shoots to our different campsites each evening. We would add an additional 7 miles or so on other connector trails to see some sights and to get to nightly campsites that weren’t right on the loop. In total we probably did about 16 miles in 4 days. A good amount for a beginner trip.
Our trip started on the Ashland-Bayfield Express which leaves to go out to the islands on Tuesday, Friday, Saturday and Sunday at 2:15 PM.  This recreational shuttle leaves for Stockton Island early each morning before making a stop at Michigan Island, a second stop at Stockton Island before returning to Bayfield.  It then turns around and makes an early afternoon run out to Oak Island on these same days to drop off campers before continuing on to Raspberry Island.
The boat arrives at Oak Island after about 45 minutes.  Arriving at Oak Island around 3:00 doesn’t give you a lot of time to get to your campsite but thankfully there are several sites within reasonable distance of the dock. At the end of your time at Oak Island you will be able to enjoy the layover on Raspberry Island as well. You’ll have 1-2 hours to either take in the lighthouse tour given by the local volunteer in full costume, or head down to the Raspberry Island Sandspit. You probably won’t have time for both.
Once the tour boat leaves you’re greeted by a ranger that lives in a cabin just up the hill from the dock.  As the shuttle charges northward towards Raspberry Island the last sounds of civilization fade away with it and the reality of your sudden isolation slowly begins to sink in.  Yes, the comforts of town are only an hour away (well, longer than that when you realize the boat won’t come back for at least 1 more day) but at least you’re not completely alone. Should a member of your group experience an emergency the ranger will generally be about a 3-5 mile hike away!  At least that’s comforting to some degree. After a short orientation, and chance to ask some questions the ranger will bid you farewell as you head to your camping destination.  There are a couple of spots right near the dock so you could ease into things by cooling your heels at this relatively less wild slice of the island.
While my daughter and I didn’t stay near the dock we did have a fairly short hike to our first overnight stay. Before heading out make sure to check out the primo Thimbleberry patches that are right across from the ranger residence. This tart berry is my absolute favorite and feeding my face with handfuls of these delectable bright red thimble-like berries is an extremely satisfying introduction to the island. Even if you’re not staying near the dock at the group site or the individual sites, the Northwest Beach and Sandspit sites are only a couple short miles away.
A 1.3 mile path leads from the group campsite near the dock to the intersection with the Northwest Beach Trail. It might be wise to use the privy near the dock before heading out. Several artifacts from an old logging camp lie in the woods not far from the group site including an old safe.  As you follow the path to the Northeast there are several ups and downs but the grades are fairly gentle.  False Solomons Seal is a common site along the side of the trail with it’s inedible speckled berries.  A little over a mile in you will discover a trail sign pointing you to the left towards campsite 4 at the Northwest Beach.  This trail angles steeply downward to lake level over a 1.4 mile stretch. Although the trail ascends slightly at first you will then lose about 300 feet. It may be a piece of cake now but in the morning on our hike out it will be an unrelenting climb.  The whole route down provides an expansive view out over a ravine to your right.  As you get lower down, there may be some downed tree limbs to skirt or climb over. Once you spot the outhouse you’ll know that you’re almost to the night’s destination.
The Northwest Beach campsite #4 may very well be the most prized campsite in the state of Wisconsin. It lies in a more exposed spot for sailboats so you have a good chance of having this little piece of Heaven to yourself. There are a couple different picnic spots to sit at and a short path leads down to a beautiful secluded half mile long beach. Sailboats can sometimes block the view of the northern sky for campers but this more exposed spot can oftentimes prevent a safe anchorage spot especially with a northwest wind. This can provide the backpacker with an amazing spot.
Just imagine as the sun sets being able to kick back on this lonely beach as the waves crash in and all of your cares in the world seem to melt away. I don’t think I’ve ever stayed in a finer campsite although there are a few others high on my list that could compete. Preparing our Backpackers Pantry freeze dried Creme Brulee was definitely the cherry on top to this fantastic day.  The beach is positioned in such a way that you have a perfect view of the northern sky if the Aurora Borealis is active.  Sometimes sailboats can block the view of the Northern lights but depending on the wind direction you’ll likely have this half mile beach all to yourself.  I don’t think I’ve ever seen so many stars all at once.  I think I could stay out here for a week and not tire of the view.  The most visible islands are Bear (straight to the north) and Raspberry straight across from the campsite. To the West lies Pt. Detour the northernmost part of the Wisconsin mainland.
Dock-Overlook Dayhike= 7 miles round trip
Returning up the Northwest Beach trail was a chore. My daughter and I labored in nearly 90 degree heat on an uncharacteristically hot day for the Apostle Islands. We needed to take several rest stops to break up the climb in the heat.  The mosquitoes would force us to shorten those breaks but fortunately we didn’t have a big problem with them on most parts of the island.  Arriving back out to the loop trail you will take a left to continue the circle.  Before you even cover a half mile back on the loop trail the turnoff for the overlook trail appears to your left.  This intersection lies close to the highest point not only on Oak Island but the highest point in the whole National Lakeshore.  We planned to visit the nice overlook of the islands on our way to the North Bay campsite where we were staying that night. The overlook trail gradually descends until reaching a loop that takes in several different vantage points of the surrounding islands.  Either fork you take will lead to a scenic vista which keeps you just behind a wooden fence protecting you from the ever eroding cliff.  Here at the overlook you are more than 100 feet above the “Big Lake” that lies below.  As a reminder of the power of Lake Superior and the massive wave action that constantly buffets these shores, a sea arch that was once visible here (the hole in the wall arch) collapsed sometime in the winter of 2009-2010.  Even without that special view it’s still one of the best overlooks in the islands and provides a towering view of Bear, Raspberry, Otter, Manitou, and Stockton Islands among others. Devils Island lies far north lurking low on the horizon like a stealthy phantom ship.
Retracing our steps for about a half mile led us to back to the intersection with the North Bay Trail.  From here the path leads just over 1 mile down to campsite #6.  The trail begins fairly flat but starts descending at a faster clip 1/3 of a mile in.  Some interesting mosses can be found at the side of the trail here.  A steep drop off to the right leads down into a drainage area.  This part of the trail offers a decent chance at spotting Black Bears.  They have been spotted along the trail and in the drainage here on and off.  The last third of a mile has a much different personality. The path turns much steeper but switch backs ease the descent.
As the case with the last campsite, an outhouse provides the first evidence that you’re almost to your goal.  It’s here where you will find numerous Thimbleberry bushes that can provide you quite the trailside snack during July and into August. After your hike, you’ve earned it.  Once you’ve passed the privy it’s a short 1-2 minute walk into campsite #6.  It’s a very busy area, much different from the Northwest Beach site #4.  It’s a well sheltered area so you will often have sailboats anchored off shore and they will be constantly coming to shore to either use the bathroom, check out the beach or walk up to the Oak Island overlook.  It’s a really nice looking campsite but more busy than the other sites on the island due to boater traffic.
We had a rather anxious night at campsite #6. First we woke up at 3:00 in the morning to my daughter feeling very ill. It wasn’t just a typical upset stomach; something just seemed not right. My mind raced back and forth about all the possible things that could go wrong and I envisioned having to walk 5 miles through the forest in the dark with only a flashlight to get help at the ranger station.  She was seeming so disoriented that I actually called out to some of the sailboats to see if anyone could radio for help. It was really a scary moment.  I don’t think I’ve ever seen her like this before. When I realized no one could hear us I was actually preparing myself for a frantic walk out to the dock in the middle of the night to get help but after praying with her and trying to decide what I should do she was suddenly feeling just a touch better. We took off the rain fly to get a little bit more air in the tent and after just sitting out at our picnic table for a half hour we retreated back to the tent.  We woke up a little later to the sound of rain and I had to scramble outside once again to get the rainfly back on the tent before the rain picked up. In a dramatic feeling of relief I realized my daughter was showing further improvement so I figured we could sort everything out in the morning.
As the sun rose, I realized her illness passed just as quickly as it arrived. We still don’t know what caused it but it’s a moment that even after the passing of time still gives me goosebumps even as I merely just write the account.  Other than some blisters starting to form on her feet though we would proceed with our adventure on this new day.  We would have to get her some better shoes for the next trip!  Campsite #6 at North Bay would have a fantastic exposure for viewing the Northern Lights if not for all the sailboats whose lights at the top of the mast wash out your view of the Northern sky.  In the morning expect to have traffic start to trickle in as people come to shore in a dinghy. Don’t get me wrong this is still a great campsite but it just gets significantly heavier foot traffic than the other sites on the island.
Proceeding to the next campsite on this clockwise loop tour of Oak Island requires your longest day yet.  This longer hike begins with a 1.1 mile hike back up to the overlook trail.  This hike is broken up into 3 distinguishable segments. The first third of the trail is a steep climb as you begin to switchback up a steep grade just after passing the outhouse. You can look out over a drainage through a ravine to your left as you climb.  The grade is significantly lessened for the middle third of the trail while you know you’re in the home stretch when the trail flattens out.  This signals that you’re only about a third of a mile from the Overlook Trail.  This time when you reach the loop trail you’ll continue on the clockwise motion turning off to the left.
You’ll quickly gain a little additional elevation and reach very near to the highest point on any of the Apostle Islands.  Oak Island is the tallest in the chain and reaches 1,081 feet, nearly 500 feet above Lake Superior.  The high point will be in the woods off to your right as you follow the trail shortly after rejoining the loop trail but there’s no awe inspiring view here due to the heavily wooded nature of the wilderness you’re traversing.  Shortly after you will begin to lose elevation on a long downhill but before you get too excited reality strikes and you begin a set of switchbacks that bring you deeper into the forest.  Talking loudly with your hiking partners could be a good practice through this lesser traveled part of the island as seeing a black bear is a very real possibility.  The wildlife doesn’t see as many humans through here. The loop trail between the overlook trailhead and the Sandspit is the least traveled segment of trail on the island.  There’s not as much to see here but it can be a humbling experience to travel through the Timbuktu of Oak Island and listen to the dead silence or the rustling of the wind through the trees.
After passing through the switchbacks the trail will level out and the understory of the forest will really open up. After passing through a series of wooden planking you might notice a funny looking device. This is actually a wildlife camera that park officials use to see what’s walking through so give the camera your nicest smile as you pass by!  As a reminder that you’re in bear country (as if you could forget) you may notice several trees with heavy scratch marks on them just before you come to an area of dense fern coverage.  As you start to get nearer to the Sand spit be on the lookout for a false trail that might try to lead you off in the wrong direction. Follow the most obvious path to stay on the loop trail. You will take a sharp right at another wildlife camera shortly before beginning a steep descent which deposits you near the Oak Island Group campsite A.
Dock-Oak Island Sandspit (3 miles Roundtrip)
The group site has closest access to the privy and the individual campsite #1 lies below. While campsite #4 at the Northwest Beach might be my favorite campsite ever for the long private beach and privacy, the sandspit site has it beat for overall scenery.  I absolutely loved the setting within an Oak Savannah (reminiscent of the one at Julian Bay on Stockton Island) and it was a joy to stay here for 2 nights and rest up before the short 1.5 mile walk back to the dock on our final day.
3 boardwalks radiate from campsite #1 out to the lake each offering a different view. Facing the lake the trail on the right goes through a mixed Oak & Pine area.  You’ll find Blueberries (in season) and Blackberries on your right and some high vitamin C Rose hips, an edible nutritious berry, to your left.  The path terminates at a part of the beach that may be under water at higher levels.  The trail down the middle goes through beach grasses and a few scattered trees as it proceeds to a west facing beach.  The view across the channel is of the Red Cliff Indian Reservation with just 1 single dim light visible across the channel after nightfall (the darker the better of course).  The trail on the left leads to a south facing beach.  The beauty of the whole setup here is that when encountering winds from the south you could retreat to the western beach and vice versa during a westerly.  Following the beach to your left provides access to a small hidden portion that you can walk out to and watch waves lap into small indented caves. The beach then yields to a pleasant looking rocky shoreline to your left.
A rogue wave nearly brought my trusty camera to an early demise. Maybe I was just distracted by the whole beauty of the place but you never let your guard down in the presence of the granddaddy of all lakes. I saw it coming just 2 seconds too late. As the wave rushed towards shore I grabbed my camera just as the remnants pushed past my ankles. Lifting it up I could tell the damage was done. A white scourge slowly swept over the whole LCD display until I wasn’t sure what I was looking at. Lesson learned. Don’t turn your back on Superior! Thankfully my camera recovered and amazingly is still working just fine!
The Sandspit was such an enjoyable place to spend a couple of days. There is definitely more to do here and look at than the other campsites so it all depends on what you’re in the mood for.  Some beach “eye candy” and berry picking with more places to walk (#1), a social hub with good access to the overlook (#6), an off the beaten path private half mile beach with excellent view of the northern sky and the darkest part of the island at night (#4) or the convenience of being close to the ranger station and dock (#2 and #3). Personally, as much as I love the sandspit and there is more to do there, I savored every minute of my stay at the northwest beach and because of the quietness, privacy and nighttime darkness there is just something about it that can’t be beat in my mind. You really can’t go wrong with any of these campsites.
Sitting out on the beach in the evening hearkens back to times gone by, a simpler time when people trusted each other and had stronger bonds.  I experienced this first hand on our 2nd to last night on the island.  A couple from Chicago and their 2 kids were anchored offshore and came to check out the sandspit.  The sheer beauty of the setting sun seemed to provide a bond between us even though we had never met.  We were able to just enjoy watching the amazing light display put on as the sun dropped below the horizon.  Their kids even came over to play cards with my daughter after dark while the parents relaxed back at their sailboat.  Such relationships between strangers seems to be more rare nowadays as everyone is conditioned to be suspicious of one another (unfortunately for good reason).  Here, it seems that the hands of time have been turned back even if just for a few days.
On the final day of our adventure we packed up our stuff for the final 1.5 mile walk to the dock.  It was a bittersweet ending to such an amazing backpacking trip.  Probably the favorite backpacking trip I’ve taken.  The island has a little bit of everything.  Before heading out go check for newly ripened thimbleberries surrounding the weather station just past the group campsite.  The trail rises and falls many times as it climbs up and over seasonal stream beds en route to Gitchee Gumee.  In some places wooden boardwalks traverse an otherwise dangerous spot over the many ravines or the occasional muddy spot.  As a final treat the sandspit trail offers up numerous views of Lake Superior as this trail never strays far from the lake.  All too soon, we reached the dock which we had left 4 days earlier.  Just make sure to allow yourself plenty of time on your following morning so you don’t sweat it out on the final stretch wondering if you will make it to the dock before the ferry boat leaves without you (they will not wait for you if you aren’t there in time).  It would be an even bigger calamity to miss the Tuesday boat as the next one wouldn’t arrive until Friday!
We had mixed emotions as we boarded the boat to return to Bayfield.  On one hand, we were sufficiently worn out after hiking nearly 20 miles between all the trails and side routes we took to explore the island. On the other hand, I was truly going to miss this beautiful wild place.  There’s something to be said about hiding in the wilderness for several days.  You may be thinking about the outside world and it’s associated worries on day 1 but if you allow yourself to move into the rhythm of island time (especially wilderness island time) you will come away energized and prepared for the inevitable worries that are waiting for you back in civilization.
Midwest Explorer 