Side Quest! – Hiking in Madeira

We are here with another special “side quest” episode! This time we are talking all about the different hikes we did in Madeira. Madeira is a Portuguese mountainous volcanic island to the southwest of mainland Portugal – it is known as the “Hawaii of Europe”. Rachel & Darren went there for their honeymoon trip in 2024 and got to experience a lot of different hikes the island is well known for.
Hikes/Places covered in this episode:
*PR8 – Vereda da Ponta de São Lourenço: Also known as the “Dragon Tail” of Madeira. This trail is rugged and arid (desert-like)! It was also the WINDIEST hike we’ve ever done to this date! The hike itself is only about 4 miles out-and-back, but we had to pick up our rental car earlier that afternoon, so by the time we made it there, parking was completely full and we ended up having to park down the road 1-2 miles from the trailhead. Bonus: There’s a little cafe at the end of this trail (before turning around and heading back)!
*Levada do Moinho to Levada Nova: This was a completely different vibe than the PR8! It was one of Madeira’s traditional “levada” trails – trails that follow water irrigation channels. The trail wanders the cliff sides of traditional farmland with the ocean at your back. Some main highlights were a double waterfall that you walk behind through a tunnel and a really long tunnel following the waterfall (make sure to bring headlamps)! Side note: If you are afraid of heights, you may want to consider out and back on Levada Moinho instead of connecting up to Levada Nova…there were some spots that definitely sketched out Rachel (haha). The trail itself is 5-5.5 miles total “loop”. This was also Darren’s favorite hike in Madeira!
*PR9 – Caldeirão Verde Levada Trail: If you hike this one, go EARLY! We got there early and there were not too many people on our way into the trail (it is an out-and-back), but on the way out, we passed SO MANY people, which made the way back not as enjoyable. Mostly because there are several spots where this trail is very narrow (running parallel to another “levada”) with drop offs on the other side, so there was a lot of maneuvering and waiting turns to pass (everyone we encountered were respectful though, which really helped). The trail is a little over 7 miles out and back and has multiple tunnels along the way and leads back to an epic waterfall – the Caldeirão Verde!
*Fanal Forest: A centuries-old laurel tree forest that is a UNESCO World Heritage site in Madeira. It is well known for its mystical atmosphere that is created by dense fog rolling through the trees. It was actually POURING rain when we went to see it for the first time, which was quite the *experience* and we would not trade it for anything! We actually ended up going back another day when it was bright and sunny and it had totallyyyy different vibes (the Shire!!). We have heard that since we were there in 2024, the island has erected fences to keep visitors on a more specific path, so I’m not sure how much freedom you really have to roam through the trees anymore…which…is a shame, but also understandable as the area was seeing a lot more tourism that it could not support.
*PR1 – Vereda do Areeiro: Okay…so we did not actually hike this one! We had plans to hike it to the “Stairway to Heaven” – an iconic mountain pass with views on either side of a narrow “stairway”, but upon starting the trail (basically inside of a cloud because of how foggy it was), Rachel immediately felt uncomfortable. It was just a combination of the extreme heights, how the land sloped off pretty steeply on either side of the trail, and the amount of people passing through. We planned to get an earlier start and be on the trail for sunrise, but our shoes were still soaking from our Fanal Forest trip the previous day, so we spent a good amount of time drying them out with a hairdryer LOL. Anyway, long story short – we turned around after just starting the trail and ended up just walking around the top area near-ish the visitor center! Which, to be fair, had EXTREMELY beautiful views AND we were able to stay away from the majority of people, which was really nice. No regrets! Sometimes you just have to listen to your body and mind. Maybe one day we will go back again and accomplish it!
*We ended our trip with a sunrise on the black sands beach of Seixal. It was the perfect ending to our trip – getting to experience a beautiful sunrise and then getting a breakfast from a local spot with the most perfect views above the beach. We then just walked around and ended up visiting a cafe that sold some local art, which was really cool and our favorite type of souvenir!

Anyway, this episode CONCLUDES our Portugal “Side Quest” series! Stay tuned for more side quest episodes that take place a little closer to home (Kentucky). ❤

As always, thank you for listening! For Red River Gorge content, follow @tread_the_red on Instagram or check out TreadTheRed.com. For side quests content, follow @ttr_sidequests on Instagram!

An Echo of a Vibe

NEW ACHIEVEMENT!! You have unlocked a new episode of Tread the Red! AWARDDDD? It features a new-to-the-podcast trail: Castle Arch! Side note – I hope you read that in the Dungeon Crawler Carl AI voice.
Anyway, as you can tell from the title and the opening of this description, this is a Rachel-Darren-Fun-Time-Adventure-Time-Gorge-Time episode! We recently (kind of) hiked Castle Arch Trail for the first time and while it was definitely an *adventure*, it was wellllll worth it! The arch itself is super cool and then the overlooks from the top of the arch are the cherry on top!
Trails featured in this episode:
*Castle Arch Trail (Unofficial)

Other Gorge things: The RRG Farmers Market is in full swing! Tread the Red set up for their opening weekend and we will be back for Memorial Day Weekend as long as storms don’t cancel the event! Tread the Red has also been taking a social media hiatus – we may post randomly when we drop a new podcast episode or for other things, but if you need to reach us, you can always contact us at treadtheredpodcast@gmail.com!
Thanks for listening and happy summer weather hiking! Stay hydrated!

Side Quest! – Funchal, Madeira

Hello Hello!! Welcome to another “Side Quest” episode of Tread the Red! We have finally made it over to Madeira – a Portuguese island! In this episode we cover our time in Funchal – the capital city of Madeira. We explore the city by foot and take a cable car up to Monte Palace Tropical Gardens! Keep an eye out for the next Madeira “Side Quest” episode because we will be getting into all the hikes we did on the island during that one! Hope everyone is having a great spring and getting outside!

$4500 Footlong Worth

We in fact did NOT get there on the actual podcast recording, but back in the day, when Subway foot longs were apparently $5, it would have cost $4,500 to fill the Nada Tunnel from entrance to entrance. In case you were wondering.
Anyway, welcome to Tread the Red! We’re a Red River Gorge Podcast that *occasionally* talks about other cool places! But this episode is a standard Rachel-Darren-Fun-Time-Gorge-Time-Adventure-Time episode. **I do want to apologize that apparently Pippin had a front row seat to the microphone while he was chewing his bone for some of this…** We talk about these cool hikes during this episode:
*Big Hole Arch (+Military Wall Trail to get there)
*Suzanna Arch Trail (Cliffview Resort Property in the RRG)
Thanks for listening to us talk about this place we love! Happy hiking!
You can follow us on Instagram/TikTok @tread_the_red
You can check out the website at TreadtheRed.com

Side Quest! – Sintra, Portugal

We’ve gone and made another “Side Quests” episode! This time we are covering our time spent in Sintra, Portugal. Even though we only took a day trip here while we were staying in Lisbon, we managed to fit in a lot! Honestly, we wished we had spent more time here than we got but we made the most of it.
We took a train from the Rossio station in Lisbon to Sintra to start the day. Sintra is the last stop, so the train ride took about 45 minutes. Once in Sintra, we booked it to Quinta da Regaleira so we could get in and see the “Initiation Well” before the crowds. This was such a good decision because a little while after we had gone through, we circled back around and saw a huuuuge line waiting their turn. We spent a good amount of time wandering through Quinta da Regaleira and managed to also see the inside of the estate while we were there as well (but in our opinion, the grounds were where the real awesome stuff was)!
After having an *interesting* lunch experience, we got a ride to the Moorish Castle grounds. We got to walk the battlements high above the city of Sintra, which was really cool, but also a little scary because it was SUPER windy.
Lastly, we went over to the Park and Palace of Monserrate. The actual palace was super cool because of its intricate and colorful architecture, and the grounds were very cool too – we found an old abandoned chapel ruins.
To learn more details, you’ll just have to listen to the episode! In summary, this episode covers:
*Sintra, Portugal: Quinta da Regaleira, Moorish Castle, Monserrate Palace

Thanks for listening! If you are new here, our “Side Quest” episodes feature places we’ve been that are *not* the Gorge…I know. Kinda confusing, but we thought people might want to hear about other places too! We haven’t finished our Portugal trip series yet, but once we do, we can get into some other hikes that are a little closer to home. 😀

A Study in Crab Walking

Welcome back to another episode of Tread the Red! It’s 2026 and we are hiking to some new-to-us places and with some cool new people! 😀
In this episode, we go on a rhodo-tunnel STEEP winter adventure down to Lower Chimney Top Falls and then make our way back up to Middle and Upper Chimney Top Falls! We ended up getting to do this hike with our friend, Jessica! You can follow her hiking adventures on Instagram @jess_took_a_hike ! There was a light coating of snow on the ground when went out to complete this trail together – which made for slippery conditions BUT it actually helped us to be able to see the “unmarked” trail a bit clearer!
The trail back to these waterfalls is one of the many unmarked/unofficial trails within the Red River Gorge, and is such a fun adventure! With that being said, you definitely want to be familiar with the area and have some maps downloaded to your phone ahead of time to help with navigation. If you want to learn more about this trail as a whole and listen to our trail shenanigans of the day (crab walking and intentional butt sliding and…some not-so-intentional sliding LOL), check out this episode!
Trails Featured in This Episode:
*Hidden Arch Trail (an “official” RRG trail)
*Chimney Top Waterfalls Trail (an “unofficial” RRG trail)

As always, thanks again for listening to Tread the Red! You can follow us on Instagram & TikTok @tread_the_red or at @ttr_sidequests (for our other non-RRG adventures). Happy hiking!

AS IF YOU COULD OUT HIKE ME

It’s officially HOA HOA HOA HOA HOA seasonnnnn. Welcome to Tread the Red Podcast – we are here to talk to you about some Red River Gorge hikes! In this episode we delve into the world of the Rough Trail and the trials and tribulations of the Eagles Point Buttress loop trail. We hope you’re having a great end of Fall/beginning of Winter hiking season! Keep an eye out on Instagram for any updates: @tread_the_red and/or follow our “Side Quests” page: @ttr_sidequests

A Hot New Bombshell Enters The…Gorge

Hi and welcome to another episode of Tread the Red Podcast! TONIGHT we talk about Rachel’s birthday in the Gorge including CABIN GOATS, a small detour to rant about cabin prices, a fantasy-themed hike (specifically dragon riders), and a trip over to the White’s Branch Arch area including a new-to-us arch and a couple overlooks!
Trails/Points of Interest Specifically mentioned:
*Tarr Ridge East/Extravaganza
*Whites Branch Arch
*Ramp Arch
*Twilight Arch and Overlooks
As always, thanks for listening and if you are interested you can follow us on Instagram and TikTok @tread_the_red or check out our website TreadTheRed.com.

Side Quests! – Lisbon Pt. 2

Welcome to Tread the Red Podcast – Darren hates poop jokes, but Rachel loves them – which team are you on?!
Anyway, you’ve stumbled upon one of our special “Side Quest” episodes! This episode features our Day 2 itinerary during our honeymoon in Portugal – specifically featuring Lisbon. We talk about the Feira da Ladra (Lisbon’s most iconic market), sight seeing in the area including the Lisbon Cathedral, the LX Factory, and Lisbon Under Stars at the Carmo Convent ruins.
We wanted to point out that we recorded this episode back in the beginning of March of this year, so there are some current event details at the beginning of the episode that are very much out of date. Sorry!! Rachel has been very bad about posting these. Oops.
We know we veer away from The Gorge during these “Side Quest” episodes, but we hope you all still love them nonetheless!
If you do, and you want to see more “Side Quest” content – you can follow @ttr_sidequests on Instagram and TikTok!
If you are like I HATE THIS CONTENT – please skip the episodes starting with “Side Quests!” and follow us on Instagram and TikTok at @tread_the_red – SPECIFICALLY Gorge content. ❤
Thank you for listening and supporting and we hope everyone is having a great summer and staying hydrated!

What Happens When Darren Isn’t There

Hi and welcome to Tread the Red Podcast! In today’s episode we talk about Rachel’s annual Gorge trip with her mom (and Pippin). Despite the episode title, Darren is the other host of this episode! We specifically talk about how things always seem to go wrong for Rachel at the Gorge when Darren isn’t part of the trip – you’ll have to listen to find out what happened this time.
The trail(s) featured in this episode are:
*Koomer Ridge Trail
*Buck Trail
*Pinch-em-Tight Trail
*Rough Trail
More specifically, we hiked a loop that encompasses all of these trails and is close to 8 miles long! We definitely recommend it if you are looking for a longer and more challenging hike. You’ll cross multiple creeks though – so be prepared (especially if water levels are higher).
We also include a short section to discuss how someone tried to impersonate us by making a fake Tread the Red Reddit account – if you saw any posts by a user “tread_the_red” on Reddit, that wasn’t us! We actually have a Reddit account called “TreadTheRed” (no underscores). We don’t really use it, but that is the real one. Anyway, we just wanted to be very clear that we had nothing to do with the fake account or any of the stupid things they were posting! We would never want to spread hate and misinformation about the Gorge like they did. ❤
Anyway, we hope everyone is having a great summer and staying hydrated! The RRG Farmers Market is in full swing and you can catch it every Saturday at the Natural Bridge chairlift lawn from 10AM-2PM. We highly recommend checking it out if you’re in the area!
Stay tuned for another “Side Quest” episode featuring our trip to Portugal – we recorded the episode MONTHS ago, so there is some outdated current event information at the beginning, just FYI.
Thank you to everyone who listens and supports us! You can follow us on Instagram/TikTok @tread_the_red