50 Unique Things to do in Weymouth and Portland

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Looking for all the very best things to do in Weymouth, Portland, and the nearby area? You need to ask a local! Lucky for you, I was born and bred in Dorset’s sunny seaside town and I have got you covered! This is a bumper post featuring all my favourite things to do in the area. From famous tourist sites to hidden gems, from quirky festivals to fab foodie tips… this is everything you need to plan the perfect trip to Weymouth.

This post is completely honest, and not affiliated with anyone. I gathered up all the very best recommendations from friends and family I trust, as well as every single thing I’ve ever discovered in my local area. These are 50 things you need to see, eat, and do in and around Weymouth. So now you can visit over and over to see it all!

Last Update: Feb 2023 with latest dates and info. 

44 Unique Things to do in Weymouth

Just before we get started, I feel like I should confess that I’ve probably been a bit loose with the term “unique” on some of these. For example, Weymouth isn’t the only place in the world with a seafood festival – but it is the only festival for local Dorset seafood. But while it’s not technically all completely unique, these really are all of my favourite things to do in Weymouth (and the nearby areas) and many of them hold a very special place in my heart.

READ MORE: The Ultimate Guide to Dorset England

(The following list is in no particular order. But I’ve colour coded the map above to help you make sense of things!)

1. Hit the Sands at Weymouth Beach

Did you know Weymouth was one of the first trendy holiday towns in the UK? When King George the Third’s doctors recommended he start sea-bathing for his health, Weymouth was the town he picked, putting our little fishing town firmly on the map as England’s royal holiday destination.

Today, the beach is a cute retro affair skirted by a beautiful Georgian terrace. Think swingboats, ice cream shops, and donkey rides – basically the very best of vintage British seaside.

2. Try a Rossi’s Ice Cream (or Six)

Welcome to the best ice cream in Weymouth! I don’t know a single local who’ll tell you otherwise. This tiny little parlour doesn’t look like much, but it is a much-loved institution in Weymouth and genuinely serves up the town’s best ice cream. Rossi’s is the best – don’t miss it.

3. Walk the River Wey

At just five and a half miles, the River Wey is the shortest major river in the UK. A lot of people don’t even know it exists, but this is the river that gives Weymouth its name. Starting in the pretty village of Upwey, you can follow the chalk stream down through some lovely countryside and into the marshlands of the Radipole Lake RSPB Nature Reserve, before finally reaching the mouth of the river – Weymouth harbour.

Download a map here

4. Stay in an Old Smuggler’s Inn

Dorset might look idyllic, but its history is full of intrigue, scandal, and smugglers! Centuries ago, the Smuggler’s Inn at Osmington Mills was a hangout for some of Dorset’s most infamous smuggling gangs. Notorious types with names like French Peter drank at the pub, and the inn was once owned by the leader of the “Charles Gang”.

Today, it’s a cosy pub at the end of one of the best cliff walks in Weymouth. It’s also one of the best places to stay in Dorset. Start at Bowleaze Cove and follow the cliff path to Osmington Mills, where the Smuggler’s Inn will be waiting for you with great local beers, tasty pub grub, and sublime views. This is also a lovely spot to stay if you don’t want to be too close to town. The inn is lovely, with pretty bedrooms and a real sense of history. I’ve stayed here once and eaten here many times, and it’s one of my favourite pubs in the area!

5. Ghost Hunting at the Nothe Fort

Voted one of the spookiest places in Britain, the Nothe Fort is a Victorian fort overlooking Weymouth harbour. It was built in 1872 and played an important role in WWII. Today it’s a lovely museum full of dimly lit underground passageways and rumours of haunting.

The best-known ghost is the “Whistling Gunner”, a restless spirit who haunts the passageways of the fort with his eerie whistling. My dad loved to scare us silly with that old ghost story – and I still can’t walk through the narrow corridors of the Nothe Fort without feeling nervous! But even if you’re not interested in ghosts, this is a great, volunteer-run museum that’s steeped in local history.

6. Spot the Cannonball in the Wall

On the corner of Maiden Street and St Edmunds Street in Weymouth town is a public loo with a pretty fascinating history. Look up and you can spot a black ball lodged in the wall. This is a cannonball dating from the 1640’s!

During the English Civil War, Weymouth was occupied by Parliamentarian troops, and in February 1645 the Royalists led a siege against them. The cannonball is a leftover from that time, most likely shot from the Chapel Fort which was captured by the Royalists. Get the full history here if you want to learn more!

7. Stroll Around Weymouth Harbour

Weymouth grew up around its harbour, and it’s a pretty historic spot. Fun fact – the Black Plague entered the UK through the ports of Melcombe Regis in 1348! Ships sailed from here to fight in the Spanish Armada, and the harbour was also the centre of much of the civil war fighting in the 17th century.

Today, it’s a picturesque spot lined with colourfully painted buildings, great pubs, and some quirky independent shops. If you want to take to the waves, there are a few boat tours and ferry services to choose from. Or for £1 you can take the rowboat ferry service across the harbour – a very cute way to hit the water! The harbour is also one of the best places in Weymouth to try your hand at crabbing. Grab a line and some bait from one of the nearby shops and see what you catch!

Where to stay – lots of the harbour-side properties are available to rent on AirBnb.

8. Best Fish and Chips in Weymouth

This was a pretty big topic of debate between me and my family and friends while I was putting this post together! In the end, I had to go all the way home just to revisit both of the top two contenders and choose the winner once and for all. Personally, I think the best fish and chips in Weymouth can be found at Fish ‘n’ Fritz – which is about a block away from the harbour.

The fish is fresh and locally sourced, the batter (a secret recipe) is superb, and the chips are chunky, soft-but-crispy perfection. I love their monthly specials – last month’s katsu curry fishcakes were amazing. And they genuinely have the best service I’ve ever received from a chip shop.

9. Visit a Pirate Graveyard

When I was a kid, the smuggling and pirate connections in Weymouth’s history fascinated me. So the ruined graveyard at the now-destroyed St Andrews Church on Portland was one of my favourite places to explore. It’s known locally as the Pirate’s Graveyard, and a few of the graves are marked with skull-and-crossbones symbols. You’ll find it next to Rufus Castle, above Church Ope Cove.

Researching for this post, I heard rumours that these markings don’t necessarily mean that pirates are laying at rest beneath them. But I’m choosing to believe!

10. Paddleboard in the World’s 3rd largest Man-made Harbour

When it was built in 1872, Portland Harbour was the largest man-made harbour in the world. As of 2016, it was still third-largest, at 520-hectares – and it’s pretty massive! Naturally protected by Portland to the south, Chesil Beach to the west and mainland Dorset to the north, the waters in Portland Harbour are generally calm all year round. Which makes this a fantastic spot for paddleboarding. Rent a board or sign up for a lesson with Weymouth Watersports, and hit the water to get a different perspective on the coastline.

11. Spend the Night in a Lighthouse

If you’re looking for unique accommodation near Weymouth, why not consider renting your very own lighthouse? The Old Higher Lighthouse on Portland features two cottages, one in the grounds and one attached to the lighthouse tower itself. Built in the 18th century, Old Higher Lighthouse is full of history and makes a seriously unique place to stay!

12. Grab lunch in the Boat that Rocks

Did you know, the 2009 movie The Boat that Rocked was mostly filmed on location in sunny Portland?! And at the end of Chesil Beach sits a fab little restaurant with a name inspired by the movie.

The Boat that Rocks is in a great spot overlooking the harbour, and it’s a much-loved local favourite. Apparently, some of the cast of the movie have been known to pop in for a meal!

13. Meet the Rescue Turtles in Sea Life Centre’s Turtle Sanctuary

One of the top tourist attractions in Weymouth is the Sea Life Centre, a huge aquarium with outdoor and indoor exhibits featuring local and exotic marinelife. Everything from the hermit crabs you can spot in Weymouth harbour, to endanged Humboldt penguins haling from South America.

It makes a great day out and is genuinely one of my favourite things to do in Weymouth. They also do lots of important rescue and rehabilitation work around the world – as well as running breeding programmes and championing education about environmental issues. CLICK HERE to check ticket prices an dbook.

For me, the highlight is the Turtle Tunnel, which is home to several rescue turtles from Florida. Accidents with boats off the coast of Florida left them with deformed shells that mean the turtles can’t swim properly, but the SeaLife Centre have re-homed them and fitted their shells with weights and/or floats to help them keep their balance. Without it, these beautiful creatures probably wouldn’t have survived.

14. Discover the Smuggling Secrets of The Fleet

Fans of the swashbuckling smuggler novel Moonfleet can’t miss a trip to The Fleet. It’s a brackish water lagoon between Chesil Beach and the mainland. Scattered along the coast, the village of Fleet is where J. Meade Faulkner’s novel was set, and you’ll spot a brass memorial to him in the now-ruined church. His story was a work of fiction, but this section of Weymouth’s coast abound with real-life stories of smugglers.

During the 18th and 19th centuries, smugglers would land on Chesil Beach on moonless nights, judging their location by the size of the shingle, then store their contraband in the calm waters of The Fleet to collect later. The whole area is wrapped in intrigue – and it’s also just a beautiful place for a walk.

15. Catch a Punch and Judy Show

Ah, that classic children’s tale of wife-beating and murder. Ok, these days the story has been updated slightly to make it less brutal than the original version – which is probably a good thing if you really look at the actual story of Punch and Judy. Either way, it’s a British seaside institution and Weymouth has one of the last beach-based Punch and Judy theatres in the country. Definitely worth a watch.

16. Visit Abbotsbury Swannery

Just along the coast, the pretty village of Abbotsbury makes a great day out from Weymouth. Along with beautiful old buildings and the remains of the 11th-century abbey which gives the village its name, Abbotsbury is home to the world’s only managed colony of nesting swans. The swannery is home to over 600 mute swans, and visitors can walk among them. Visit between mid-May and the end of June to see cygnets hatching!

17. Stay in a Georgian B&B

Many of the hotels along the Esplanade in Weymouth date from the Georgian period, when King George III began holidaying here and tourism took off in our lovely little seaside town. Until that time, most of the buildings on the seafront faced inland, their backs to the water. After tourism and sea-bathing became more fashionable, the buildings began to make an about-turn to face the ocean.

A Georgian-era B&B on Weymouth seafront is the perfect accommodation choice if you want to be close to the beach. My personal recommendation is B+B Weymouth; I’ve stayed there before and it was clean, comfy, and quiet – and directly opposite the beach. Perfect!

18. Check the Time on the Jubilee Clock

The red, blue and gold Jubilee Clock was built in 1888 to celebrate Queen Victoria’s Golden Jubilee. It’s stood proudly on the seafront ever since and is now a Grade II listed building – and a Weymouth icon. It’s also one of the most wonderfully British looking things I’ve ever seen!

19. Visit Portland Bill Lighthouse

Another iconic Grade II listed building is the Portland Bill Lighthouse, which dates from 1906 and stands proudly at the edge of a  dramatic cliff. Portland Bill itself is a must-visit when you’re in the area; the beautifully rugged and rocky tip of the island is a great spot to watch the waves crashing against the cliffs. Visitors can explore the old Keepers’ Cottage to learn more about the history of the lighthouse, and climb the tower itself for a fabulous view of the Dorset coastline.

20. Glamp on a Vineyard

England’s wine scene has really taken off in recent years, and the south has a few dozen vineyards. Dorset itself has several, and Weymouth is home to the artisanal Portesham Vineyard. You can visit the vineyard for tours and tastings, or for a truly unique experience you can actually glamp on-site in the vineyard’s boutique shepherd’s hut. It looks like a truly beautiful experience if you’re looking for accommodation with a difference.

Confession – this is one of the few things on my list that I haven’t actually tried myself – but the awards speak for themselves. And I intend to visit for a wine tasting when I’m next at home – so I’ll keep you posted!

21. Walk Along Chesil Beach

If you went to school in England, you may well have seen Chesil Beach in your geography textbooks. It’s a pretty unique “barrier beach”, a 29km long strip of shingle beach connecting the isle of Portland to the mainland. Geographically it’s significant, as one of just three shingle structures in the UK, but more importantly, Chesil Beach is a really pretty place for a walk! Starting at Abbotsbury, it’s possible to walk along the beach all the way to Portland, with the sea on either side of you.

22. Discover Sandsfoot Castle

For as long as there’s been a harbour between Weymouth and Portland, there’s been a risk of attack from the sea. In 1539, Sandsfoot Castle was built in Weymouth – almost directly opposite Portland Castle – to provide defence.

Today, it’s a crumbling ruin compared to Portland’s still-intact castle, but it’s in a gorgeous location with some fab views, and it’s also a great spot to explore with kids or history buffs. Fun fact – the castle was bought in 1902 for just £150!

23. Visit the White Horse

On the hill at Osmington, a huge white horse carved into the limestone stands overlooking the town of Weymouth. It depicts King George III – the town’s favourite patron – and it’s the subject of a bleak local legend.

Rumour has it that the artist who created the White Horse in Weymouth realised too late that he’d drawn King George riding away from the town. Worried that it would be seen as an insult, he killed himself rather than face the king.

But when King George next visited, he loved the hill figure and asked to meet the creator – and was disappointed to learn that he couldn’t. I can’t promise you that’s a true story, but it’s one almost every local seems to know!

24. Walk the Rodwell Trail

Follow the trail of an abandoned railroad which once ran from Weymouth to Portland. Along the way, the Rodwell Trail passes the leftovers of station platforms, and runs through red brick tunnels. These are the only relics of a once-busy railway line that ran here between 1865 and 1965. When I was a kid my dad convinced me that a ghost train runs through those tunnels at night. Probably not true, but I still can’t walk through them without a shudder!

25. Fossil Hunting at Ringstead Bay

Just up the coast, Ringstead Bay isn’t technically in Weymouth but it’s close enough for a great day trip. Surrounded by dramatic cliffs, Ringstead Bay is a beautiful spot with lovely views and a great coastal path. It’s also a prime spot for some fossil hunting on Dorset’s famous Jurassic Coast. With various clay beds to explore, the area is rich in fossils – mostly from the Upper Jurassic period.

26. Discover a Victorian Brewery

Brewers Quay used to be one of the best tourist attractions in Weymouth. Formerly a busy Victorian brewery, the impressive red brick building once contained a variety of unique independent shops and cafes – as well as a much-loved museum called the Timewalk.

Sadly, most of that is gone now (the council sold the building a few years ago), but the brewery itself still stands and it’s still one of the most attractive buildings in Weymouth. It’s also still home to the Weymouth Museum. Their exhibitions are packed full of interesting artefacts, and detail the history of the town. I’m pleased to announce that the museum will also remain even after the rest of Brewers Quay is converted into flats!

27. Eat the Best Local Seafood at Crab House Cafe

A local favourite in Weymouth, the Crab House Cafe comes very highly recommended! We’re very proud of our seafood in Dorset (rightly so), and if you want to sample some of the best, freshest crab in the area this is the place to come. A colourful, casual restaurant overlooking Chesil Beach, Crab House Cafe has amazing views and a seriously enticing menu.

It’s all about the crabs, of course, which are locally caught, boiled, then stir-fried in garlic, chilli, ginger and herbs. But the Crab House Cafe also have their own oyster beds – and serve the delicacy super fresh, within minutes of leaving the water.

28. Explore Portland Castle

Twinned with Sandsfoot Castle (mentioned above), Portland Castle was also built in the mid 1500’s by King Henry VIII and was considered one of his finest coastal forts. Unlike it’s twin, Portland Castle is still in pretty good nick, and has been lovingly restored as a museum making for a fab family day out. It’s also a pretty unique place for weddings (my little sister got married here) and has lovely views across Portland Harbour to Weymouth.

29. Hike along Bincombe Bumps

Weymouth might be best associated with Georgian seaside history and Victorian tales of smuggling, but history around here goes much further back. As you enter the town you drive over the South Dorset Ridgeway, and from the crest of the hill you can spot some of the Bronze Age burial mounds overlooking the village of Bincombe – known locally as the Bincombe Bumps. In recent years there have been some important archaeological discoveries around the area, so it’s a great place for a walk if you’re interested in prehistory. Or even if you’re not – since the views from up here are lovely!

30. Make a Wish at the Upwey Wishing Well

Thanks to a local tradition born in the early 20th century, the natural spring that is the source of the River Wey is called the Wishing Well. You fill a glass with water from the spring, take a sip, then throw the rest backwards over your left shoulder while making a wish. My best friend growing up lived across the road from the well, so I’ve made many a wish here. Pretty certain at least one of them was to become a writer – so maybe those waters work! I can also highly recommend the Wishing Well Tearooms, which are lovely and set within some beautiful water gardens.

31. Jurassic Coast RIB Ride

Want to get the adrenaline pumping, and see a little more of Dorset’s famous Jurassic coastline? Take a RIB Ride from Weymouth Harbour! You can find several companies along the harbour offering fast-paced RIB rides either to Portland, or along the coast as far as Lulworth and Durdle Door. It’s a great way to see the coastline from a whole new perspective.

32. Coasteering on Portland Bill

Speaking of adrenaline-pumping activities – why not make the most of Portland Bill’s natural rocky playground with a go at coasteering? Portland Bill is a world-famous climbing destination, with a huge range of cliffs to suit all abilities. Coasteering combines climbing with jumping, swimming, and other activities as you scramble through the waves, over rocks, and into some of the many caves dotted along the Bill.

33. Discover the Portland Batteries

Also on Portland is the Verne High Angle Battery; a former 19th-century gun battery found at the top of the island. It may not look like much, but the Grade II listed site is pretty historic, built in 1891 to protect Portland’s harbour and naval base. It was also used to store ammunition during WWII ready for the D-Day landings, as Weymouth harbour was one of the launch sites. Today, the batteries are a great place for a walk – with lovely views of Portland – and you can still enter many of the underground passageways (if you dare – I’m usually too creeped out). It’s also a fantastic spot for a game of hide and seek!

34. Eat at Billy Winters

Billy Winters is a cafe on the beach in Portland harbour, and comes highly recommended by numerous locals – chief among them my dad! Apparently a bit of a hidden gem, Billy Winters is known for its great food and gorgeous views of Chesil Beach. This is a lovely spot in the evening with a glass of wine as the sun goes down.

Photo Credits: Billy Winters

35. Catch a Show at Weymouth Pavilion

For faded glamour and vintage seaside charm, head to Weymouth Pavilion, which stands on the pier between the beach and the harbour. Built in 1908, this historic building holds a soft spot in many local’s hearts – I even performed on the stage here a few times as a teenager, back when I still thought I could sing! As well as a rich history, Weymouth Pavilion also has a pretty good line up of shows, especially during summer, with many that are perfect for families and young kids.

Since it lost funding from the local council, the Pavilion is now being run by a community of volunteers, so a visit will be helping to preserve a slice of local history.

36. Explore an Outdoor Sculpture Park at Tout Quarry

Did you know that St Paul’s Cathedral in London was built from limestone quarried on Portland? Sir Christopher Wren was a local MP, and his use of Portland stone popularised the quarries – so many London buildings are made of our local limestone.

As a result, the island is dotted with old quarries. One of them, Tout Quarry, is now open to the public as a sculpture park and nature reserve. Take a stroll through the maze-like gullies of the old quarry and you’ll spot all kinds of stone sculptures produced by both well known and emerging artists. This is probably one of the most unusual things to do in Weymouth and Portland, so it’s well worth a visit!

37. Have Lunch in Prison

Looking for a lunchtime spot that’s a little bit different, and that helps the local community? Head to the Jailhouse Cafe at The Verne Prison on Portland. Run by charitable company Expia, the cafe is staffed by risk-assessed prisoners on day release. It’s all about giving prisoners real work experience and training. This helps prepare them for release and gives them skills to find work after prison. Food tends to be simple classics like cod and chips, but it’s all well prepared and the views from the cafe are lovely.

38. Explore the Sculptures at Sandworld

One of my favourite things to do on Weymouth Beach is to pay a visit to the sand sculptures, which have been built on the seafront for decades. Started by Fred Darrington in the 1920s, and continued by his grandson Mark Anderson, the sand sculptures can be found directly opposite the Alexandra Gardens and change regularly. So there’s always something new to discover.

In 2011, Mark Anderson co-founded SandWorld in Lodmore Park.  It’s a unique gallery filled with sand sculptures by a variety of artists. Especially popular with families and young kids, SandWorld is a very cute day out.

39. Soak Up the Smuggling History at Moonfleet Manor

I’ve already mentioned The fleet in Weymouth and its fascinating smuggling connections. Well, if you really want the full experience you need to explore Moonfleet Manor hotel.

This Georgian manor lends its name to Faulkner’s classic novel Moonfleet, and was owned by the Mohune family immortalised in the swashbuckling story. The story in the book might be fiction, but the village, the family, and the tales of smuggling along The Fleet are very real.

Today, Moonfleet Manor is a luxury hotel known for its quirky colonial decor and gorgeous coastal views. Book in a stay, or simply stop by for a lavish afternoon tea and a nosy around the historic property.

CHECK PRICES: Hotels.com  |  Booking.com

40. Take a Day Trip to Abbotsbury

I’ve already mentioned the Abbotsbury Swannery above, but this beautiful village is close enough to Weymouth to be the perfect day out. So it definitely deserves a mention in its own right. Surrounded by picturesque countryside and filled with pretty stone buildings, Abbotsbury is a textbook “English countryside village” and makes a gorgeous day trip. It’s even possible to walk there from Weymouth along the Jurassic Coastal Path.

According to my friend Ruth, the Abbey House tea rooms in Abbotsbury are the best in the local area. Their cream teas are lush, and apparently you must not miss their pudding “the pigs delight”. There are also plenty of other tearooms and pubs to choose from, as well as several galleries and studios to explore in the village.

41. Step Back in Time at the Tudor House

For such a small town, there’s a surprising amount of history to discover in Weymouth. One of my favourites is Tudor House, a small merchant’s property near the harbour. Lovingly restored, the museum is furnished as a 17th century home. This is a great way to learn more about the history of Weymouth, and to get a glimpse of what life was like in Tudor times.

42. Catch the Views from the Jurassic Skyline Tower

Still a relatively new addition to the seafront, the Jurassic Skyline Tower is often listed among the best things to do in Weymouth. The 53-metre high observation tower stands on the pier overlooking Weymouth Beach, and rotates a full 360 degrees.  That means you’ll get some incredible views of the nearby coastline. Apparently, on a clear day you can see all the way to Durdle Door!

UPDATE: Unfortunately, the Skyline Tower has now closed. I’ll find something else awesome to add in its place, so watch this space! 

43. Rent a Georgian Seaman’s Cottage

If you’re looking for a unique place to stay in Weymouth, head to AirBnb for a chance to rent a historic local property. My favourite find is this Georgian Seaman’s Cottage on the Isle of Portland. A big stone house with lovely sea views and some original features? Sounds like the perfect place to stay to me!

Oh – and if you use my AirBnb link to sign up you can get £25 off your first booking. You’re welcome!

6 Unique Weymouth Festivals

There are tons of great festivals and events on in Weymouth. From village fetes and seaside carnivals to music and foodie festivals, there’s so much on offer. Get the full line up of festivals and events here to help plan your next trip to Weymouth!

44. Catch the Weymouth Carnival

There’s surely nothing more British than a summer carnival. So many towns across the country have one; chintzy retro affairs with bunting and street parades that celebrate all the most quintessentially British things. Like carrying on with summer events no matter what the weather does!

In Weymouth, our carnival takes place on the third Wednesday of August and it’s beloved by both locals and tourists. With a funfair on the seafront, fireworks at night, and a procession featuring the annual Carnival Queen, there’s a lot going on. But the highlight is the spectacular show from the RAF Red Arrows – one of my favourite British institutions!

2023 dates: The carnival has been postponed for the last few years. There are currently plans to bring it back for 2024, so stay tuned!

45. Nyetimber Dorset Seafood Festival

Weymouth began life as a fishing town, and we still have some incredible seafood – as well as excellent local produce! The annual Dorset Seafood Festival is one of my highlights of the summer. I mean, what’s not to love about a festival with that name?!

It takes place right along Weymouth Harbour every summer, so you can literally see where your food is coming from. This is a celebration of the very best of local produce – not just seafood but cheeses, chutneys, and locally made liquors (like my favourite, Dorset Conker Gin).

Next dates: 9th & 10th September 2023

46. Enjoy the Quayside Music Festival

A celebration of local music and talent, the Quayside Music Festival takes place around Weymouth Harbour every bank holiday. With a large stage overlooking the harbour, this is a pretty unique spot for a music festival. There are also outdoor bars and food stalls dotted along the quayside, and a great atmosphere. Oh, and it’s totally free! Not a bad way to spend a weekend…

2023 dates: all bank holidays in 2023

47. Greenhill Gardens Live Music

Right on the seafront at Greenhill you’ll find some attractive gardens, fronted by brightly coloured beach huts and home to some lovely, ever-changing flower displays. The floral clock here was built in 1936 by the same company who designed the more famous version in Edinburgh’s Princess Street Garden. All summer long, Greenhill Gardens host live music events on Sundays – perfect for a lovely, relaxed afternoon in the sunshine!

48. Watch Motocross on the Beach

Every autumn, Weymouth Beach hosts the annual Beach Motocross event run by the Weymouth & Portland Lions Club. Surprisingly, motocross was invented in the UK, so there are many tracks across the country. But very few can be found on beaches, making this a pretty unique event! It’s also the biggest amateur motocross event in the UK – with over 300 riders taking part.

Next dates: TBC (usually around October) – keep an eye on their Facebook page for updates.

49. Watch the Weymouth Yacht Regatta

With such an amazing coastline, the gorgeous bay, and Portland’s enormous harbour, it’s no surprise that Weymouth is hot on watersports. The sailing events for the 2012 London Olympics were held here for a reason!

Our annual yacht regatta is a must for sailing enthusiasts! Coordinated by the town’s four sailing clubs, the regatta is open to any yacht of size or class. There are also after-race festivities and the Sunday evening prize-giving right on the harbourside, with a fantastic atmosphere!

Next dates: TBC (usually July – check their website for updates)

50. NYE Weymouth Seafront

It might surprise you to learn that Weymouth’s New Years Eve celebrations have been ranked among the best in Europe. Most years there are over 20,000 participants, so this is one of the biggest fancy dress parties in the UK.

The main event is Front Live. All the bars along the seafront come together under a joint ticket, and spill out onto the Esplanade for an enormous street party with live music and DJ sets. This is the perfect way to round off a year of enjoying all the amazing things to do in Weymouth!

Planning Your Trip to Weymouth

Check out We Are Weymouth for more information, including helpful tips, what’s on guides, inspiration, and more.

I also want to say a massive thanks to my dad, for filling my head with useless historic facts about Weymouth and my heart with a passion for my hometown! Also to the rest of my family, and my bestie Ruth, for their help in putting this post together.

Accommodation

There are so many excellent B&B’s, guest houses, and hotels in and around Weymouth to choose from! I’ve mentioned a few of my favourite finds in this post, but there are plenty more options. Check out my guide to the best places to stay in Dorset for some more top tips! 

As always, I recommend searching on hotels.com to find the best price – I love their fab rewards programme. 

Food

I’ve touched on food a little in this post, but Weymouth has an awesome foodie scene thanks to Dorset’s amazing local produce. Especially the fabulous seafood.

READ MORE: check out my Dorset gin round-up to see what you have to drink while you’re in town!

Explore More of Dorset

NEW SITE: I recently launched a brand new website dedicated entirely to travel in Dorset. It’s going to be packed full of local knowledge, awesome things to do, and more. So go check out my new Dorset Travel Guide for more inspiration!

Only got one day? I also have a one day guide to Weymouth’s top attractions that might suit you better. 

If you want to discover more of the local area, check out these posts:

50 unique things to do in Dorset

Ultimate Dorset coast road trip itinerary 

Have I missed any of the best things to do in Weymouth and Portland? Whether you’re a Weymouth lover or a born-and-bred local, I’d love to hear your suggestions. Scroll down to leave a comment!

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