Main Street (Jamestown) - Image 1
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Main Street Jamestown

4.3
·48 reviews·Jamestown, Saint Helena, Ascension and Tristan da Cunha

Jamestown, St Helena's colorful capital, offers historic charm, breathtaking views from Jacob's Ladder, and vibrant community markets.

Highlights

Highlights

Must-see attractions

Social content

Social

From TikTok & Reddit

Best Time

Friday evenings

Live music & good eats

CrowdMedium
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Main Street (Jamestown) - Image 1

Main Street Jamestown

Best Time

Friday evenings

Live music & good eats

CrowdMedium
Highlights

Highlights

Must-see attractions

Jamestown, St Helena's colorful capital, offers historic charm, breathtaking views from Jacob's Ladder, and vibrant community markets.

4.3
(48 reviews)

"The staff are super friendly and helpful. They can’t do enough for you."

Vertical photo
TIP

👟 Conquer Jacob's Ladder

Take on the 699 steps for amazing views! Bring water and wear good shoes.

🎶 Enjoy Live Music

Check out Friday evenings for live tunes and good vibes on Main Street.

Third hero image

Highlights

Discover the most iconic attractions and experiences

Jacob's Ladder Ascent

Jacob's Ladder Ascent

Jamestown

Climb 699 steps for panoramic views of Jamestown's colorful architecture and harbor.

Jamestown Street Market

Jamestown Street Market

Main Road, Jamestown

A vibrant hub of local culture, music, food, and entrepreneurship. A true community gathering.

Historic East India Company Barracks

Historic East India Company Barracks

Jamestown

Stay or explore this beautifully restored 18th-century barracks, now a charming hotel.

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Planning Your Visit

Embrace the Steps: Jacob's Ladder

Conquer the iconic 699 steps of Jacob's Ladder for breathtaking Jamestown views. It's a challenging but rewarding climb, offering a unique perspective of the colorful capital. Wear comfortable shoes and bring water!

Jamestown's Vibrant Markets

Experience the heart of Jamestown at its street markets. These events are a fantastic way to soak in local culture, enjoy live music, and discover unique crafts and flavors. Check local listings for dates and times.

Best Times

When
Friday evenings
Why
Live music & good eats
Crowd
Medium
When
Market days
Why
Vibrant local culture
Crowd
High

Insider Tips

from TikTok, Instagram & Reddit

Exploring Jamestown (St Helena's capital) is a colourful adventure. Its 'Wotalotigot' hues are best admired from a bird's eye view atop Jacob's Ladder. @St Helena Tourism @BigAmbitions_ #StHelena #StHelenaIsland #Jamestown #island #adventuretravel #hikingadventures
@eagerjourneys
6.5K likes • 307.8K views

👟 Conquer Jacob's Ladder

Take on the 699 steps for amazing views! Bring water and wear good shoes. TikTok

🎶 Enjoy Live Music

Check out Friday evenings for live tunes and good vibes on Main Street. Instagram

How is this place even real?! Yes, Jamestown and Half Tree Hollow on St. Helena are connected by both the historic Jacob's Ladder, a staircase of 699 steps, and the vehicular Ladder Hill Road. Half Tree Hollow, a suburb of the capital, was developed above Jamestown due to limited space in the valley and is situated at the top of the hill that Jamestown sits at the base of. #sthelenaisland #jamest...
@campsbaygirl
4.6K likes • 327.5K views
🛍️✨ Jamestown Street Market Brings Colour, Culture & Community – 26 July 2025 📍 Main Road, Jamestown | #JamestownConnectEvents The heart of Jamestown was alive with music, flavours, and laughter on Saturday 26 July as locals gathered for the Jamestown Street Market — a vibrant celebration of community spirit and entrepreneurship. From 9 AM till 12pm, Webersvallei Rd transformed into a buzzing hu...
jamestownconnect
20 likes • 359 views

☕ Winston's Coffee Shop

Grab a coffee at this cozy spot on Main Street, open Wed-Sat mornings. Instagram

🎁 Visit the Magic Cave

A volunteer-run gem on Main Street, perfect for a donation-based visit. Instagram

Live from the Patio is here all September long. 🎶✨ Every Friday from 6–9PM, enjoy live music, good eats, and Main Street Jamestown charm. Don't miss it!
jamestownhotel
19 likes • 904 views

Tips

from all over the internet

👟 Conquer Jacob's Ladder

Take on the 699 steps for amazing views! Bring water and wear good shoes. TikTok

🎶 Enjoy Live Music

Check out Friday evenings for live tunes and good vibes on Main Street. Instagram

☕ Winston's Coffee Shop

Grab a coffee at this cozy spot on Main Street, open Wed-Sat mornings. Instagram

🎁 Visit the Magic Cave

A volunteer-run gem on Main Street, perfect for a donation-based visit. Instagram

📶 WiFi Password

Keep your WiFi password handy; you'll need to re-enter it often. Reddit

What Travellers Say

4.3
(48 reviews)

Reviews Summary

Visitors consistently praise the exceptional friendliness and helpfulness of the staff at Jamestown accommodations, particularly the Mantis Hotel. The historic charm of the buildings and the unique island atmosphere are major draws. While the internet can be inconsistent and dining options are somewhat limited, the overall experience is highly positive, with many guests eager to return.

"The Mantis hotel on St Helena is great place to stay. We just spent 8 nights with them. The staff is so friendly and accommodating. They even had a cake for me on my birthday. Breakfasts were included and good. They also offered lunch and dinner and food was ok. The internet situation wasn’t ideal but it was good when it worked in the room. We had to ask for new passwords quite a few times. Aside from that, it’s the best hotel to stay while in the island."

Kathy Smee

"I ate at the hotel during my last visit. (Last week) Despite the hotel just having a new manager parachuted in and very little staff at the time, the manager made extra effort to make sure our dinner guests were kept engaged while getting our meals out.
Food was good and enjoyable in comparison to some other venues, pudding choices were very limited was the only observation even with very low numbers using the restaurant.
The new manager seems keen to improve the service on this occasion he was very apologetic for the already reasonably good service.
A recommendation would be to make the restaurant attractive to local people, better advertising locally as the hotel services is kind of unknown for the period I was in town."

Johnny Clingham

"This was my second stay at the Mantis (for work reasons) and I would happily come back again. My room was very comfortable. The real highlight was the very friendly staff."

Andrew Tipping

What People Like

Friendly and accommodating staff
Historic charm and unique atmosphere
Comfortable and clean rooms

What People Dislike

Inconsistent Wi-Fi
Limited dining variety

Frequently Asked Questions

🚇 🗺️ Getting There

Access to Jamestown, St Helena is primarily via the RMS St Helena passenger ship or by air to St Helena Airport (HLE). Flights are limited and often connect through Johannesburg. Once on the island, taxis or pre-arranged transfers are available to reach Jamestown. TikTok

Jamestown is a compact capital, and much of it is walkable. For reaching higher points like Jacob's Ladder or exploring further afield, taxis are the main option. Some areas are connected by roads like Ladder Hill Road. TikTok

If you arrive by air, car rental is an option, but navigating Jamestown's narrow streets and steep inclines can be challenging. Taxis are often more convenient for exploring the town itself. TikTok

Walking is ideal for exploring the main streets and historic areas of Jamestown. For ascents like Jacob's Ladder or reaching higher suburbs, be prepared for stairs or use local taxis. TikTok

Yes, many hotels and local operators in Jamestown can arrange tours of the island, including historical walks and scenic drives. Reddit

🎫 🎫 Tickets & Entry

Jamestown itself is a public area, so no tickets are required to wander its streets. However, specific attractions or accommodations within Jamestown may have their own entry fees or booking requirements. Instagram

Opening hours vary greatly. Markets have specific times,Instagram while shops like Winston's Coffee Shop have set hours.Instagram The Magic Cave is volunteer-run and has variable hours, often advertised on Facebook. Instagram

Jacob's Ladder is a public staircase and does not have an entry fee. It's a free, albeit strenuous, way to experience Jamestown. TikTok

Room rates at the Mantis Hotel can vary based on season and room type. It's best to check booking websites or contact the hotel directly for current pricing. Reddit

Absolutely! Exploring the colorful streets, climbing Jacob's Ladder, and enjoying the general atmosphere of Jamestown are all free activities. Visiting local markets can also be done without purchasing anything. TikTokInstagram

🎫 🧭 Onsite Experience

Explore the historic streets, climb Jacob's Ladder for stunning views, visit local markets for crafts and food, and enjoy the unique atmosphere of this island capital. TikTokInstagram

Jacob's Ladder is a must for the views, the historic architecture of the 18th-century barracks (now the Mantis Hotel), and the vibrant Jamestown Street Market. TikTokInstagram

While Jamestown itself is a town, the iconic Jacob's Ladder offers a significant 'hike' with its 699 steps. For more extensive hiking, you'd need to explore areas outside the immediate town. TikTok

Capture the colorful buildings from street level, or ascend Jacob's Ladder for panoramic shots. Early morning or late afternoon light can enhance the vibrant hues. TikTok

Jamestown's historic nature, with steep inclines and many steps (like Jacob's Ladder), can present challenges. The main street is relatively flat, but exploring beyond that may require assistance or alternative transport. TikTok

🍽️ 🍽️ Food & Dining

Dining options include the Mantis Hotel restaurant, which offers breakfast, lunch, and dinner.Reddit Local cafes like Winston's Coffee Shop are great for a morning pick-me-up,Instagram and street markets offer diverse food stalls. Instagram

You can find a mix of local and international cuisine. Hotel restaurants offer varied menus, while markets provide local snacks and dishes. InstagramReddit

While options might be limited, restaurants are often willing to accommodate. Informing staff in advance about dietary needs can help secure suitable vegetarian meals. Reddit

Many hotels in Jamestown, including the Mantis Hotel, include a copious breakfast with a variety of choices in their room rates. Reddit

Yes, Winston's Coffee Shop on Main Street is a popular spot for coffee, serving from Wednesday to Saturday mornings. Instagram

📸 📸 Photography

The colorful buildings lining Main Street, the panoramic views from the top of Jacob's Ladder, and the bustling Jamestown Street Market offer fantastic photographic opportunities. TikTokInstagram

Early mornings and late afternoons often provide the best light for capturing the vibrant colors of Jamestown, minimizing harsh shadows and creating a warm glow. TikTok

As with any public place, be respectful when photographing people. It's always polite to ask for permission, especially if you plan to use the photos commercially. Instagram

Drone regulations can be strict, especially on islands. It's advisable to check with local authorities or your accommodation regarding drone usage before flying in Jamestown. TikTok

A versatile lens (like a 24-70mm equivalent) is great for street scenes and wider shots. A wider lens can be useful for capturing the scale of Jacob's Ladder. A smartphone is also excellent for quick snaps. TikTok

For Different Travelers

Tailored advice for your travel style

👨‍👩‍👧 Families with Kids

Jamestown offers a unique adventure for families, though it requires some planning. The climb up Jacob's Ladder is a memorable challenge, but consider if it's suitable for very young children or those with mobility issues; the road alternative is available. TikTok The Jamestown Street Market is a fantastic place for kids to experience local culture, with potential for fun food and crafts. Instagram Accommodation like the Mantis Hotel is generally family-friendly, offering comfortable rooms and helpful staff. Reddit Pack plenty of snacks and water, especially if tackling the ladder, and be prepared for a slower pace of exploration.

🚶‍♀️ Solo Travelers

Jamestown is a welcoming destination for solo travelers. The friendly staff at accommodations like the Mantis Hotel make it easy to feel at home, and they can often assist with arranging tours or providing local insights. Reddit Climbing Jacob's Ladder offers a personal challenge and rewarding views. TikTok Engaging with local markets and events is a great way to connect with the community and experience the island's unique charm. Instagram Be prepared for potentially spotty Wi-Fi, but embrace the opportunity to disconnect and enjoy the surroundings. Reddit

💰 Budget Travelers

While St Helena can be a pricier destination due to its remoteness, Jamestown offers some budget-friendly options. Exploring the town on foot, climbing Jacob's Ladder, and browsing local markets are free activities. TikTokInstagram Look for guesthouses or self-catering options if available, as hotels like the Mantis can be more upscale. Reddit Eating at local eateries or market stalls can be more economical than hotel dining. Researching transport options in advance is also key to managing costs.

Deep Dives

In-depth insights and expert knowledge

The Iconic Jacob's Ladder

Jacob's Ladder is more than just a staircase; it's a landmark and a rite of passage for visitors to Jamestown, St Helena. This historic 699-step climb connects the lower town with the upper settlement of Half Tree Hollow. Built in 1825, it was originally used by soldiers and residents to access the higher ground. Today, it's a popular challenge for tourists seeking unparalleled views of the town and harbor. The ascent is steep and can be demanding, so it's crucial to wear comfortable footwear and carry plenty of water. The reward, however, is a breathtaking panoramic vista that truly captures the unique geography and colorful architecture of Jamestown. TikTok+1

For those who prefer not to tackle the stairs, Ladder Hill Road offers a vehicular alternative to reach the top. This road also provides scenic overlooks, though the direct experience of climbing the ladder is often considered a highlight of a Jamestown visit. Whether you climb it or drive it, the perspective from the top is unforgettable and offers a different appreciation for the town's layout and its strategic position. TikTok

Jamestown's Vibrant Community Life

Jamestown pulses with a strong sense of community, often showcased through its lively street markets and local events. The Jamestown Street Market, held on Main Road, is a prime example, bringing together locals and visitors for a celebration of culture, entrepreneurship, and good cheer. These markets are a fantastic opportunity to sample local delicacies, discover handmade crafts, and enjoy live music, creating a vibrant atmosphere that reflects the island's spirit. Instagram

Beyond the markets, Jamestown's social scene includes regular live music events, particularly on Friday evenings at venues like the Jamestown Hotel's patio. These gatherings offer a chance to experience local talent and enjoy the town's charm. Even smaller establishments like Winston's Coffee Shop contribute to the community feel, serving as local gathering spots. Instagram+1 The presence of volunteer-run attractions like the Magic Cave further highlights the community's dedication to creating unique experiences for visitors. Instagram

Historic Charm: The Mantis Hotel

The Mantis Hotel in Jamestown is a testament to the island's rich history, ingeniously repurposed from 18th-century East India Company barracks. This upscale accommodation offers a unique blend of historical ambiance and modern comfort, providing guests with a refined stay right in the heart of the capital. The hotel's location is central, yet it maintains a quiet atmosphere, allowing guests to immerse themselves in the historic surroundings. Reddit

Guests consistently praise the hotel's friendly and accommodating staff, who go the extra mile to ensure a pleasant experience, even arranging special touches like birthday cakes. The rooms are described as very clean, comfortable, and serviced daily, with thoughtful additions like homemade energy balls. While the internet can be a bit temperamental, requiring frequent password re-entry, the overall service and hospitality make it a standout choice for accommodation in Jamestown. Reddit

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