Essex, on London’s northeastern doorstep, blends Roman Britain, Saxon strongholds, and North Sea horizons. Colchester—Britain’s first recorded town—still wears its history: a Norman keep, Roman walls, and a museum packed with Iron Age treasure. Along the coast, Southend-on-Sea’s pier (the world’s longest pleasure pier) and Leigh-on-Sea’s cockle sheds serve old-school seaside charm.

Inland, painter John Constable immortalized the willows and water meadows of Dedham Vale. Maldon’s salt, Mersea’s oysters, and orchards around the Chelmer & Blackwater Navigation shape a food scene that’s proudly local. Expect award-winning pubs, tearooms run by jam royalty, and seafood shacks that let the day’s catch do the talking.

Practical notes: London Stansted sits within Essex; London City, Gatwick, and Heathrow also work. Trains are frequent via Greater Anglia and c2c; buses cover the gaps. If you plan Mersea Island, note “The Strood” causeway can flood at high tide—check times. Weather shifts quickly on the coast: layers, a light rain jacket, and comfy walking shoes go far.

How to get there: Fly into London (Stansted is closest). Compare flights on Trip.com or Kiwi.com. For UK trains (including London–Essex routes), search and book on Omio.

Colchester

Colchester is ancient Britain in high definition. The massive Colchester Castle—built atop a Roman temple—anchors a compact center filled with Tudor lanes, indie coffee bars, and a lively arts scene (Firstsite has award-winning architecture and smart exhibitions). The town makes an easy base for Constable Country and Mersea Island.

• Top sights: Colchester Castle & Castle Park, Roman Wall and Balkerne Gate, Firstsite contemporary art gallery, Colchester Zoo (not just for kids), and the Roman Circus Visitor Centre.
• Eat & drink: The Old Siege House (historic beams, British-French plates), Grain (creative small plates), North Hill Noodle Bar (pan-Asian comfort), and Two Brews (third-wave coffee and pastries).
• Stay: Browse Colchester stays on VRBO or hotels on Hotels.com. Look near the High Street for easy walking to sights.

Day 1: Arrival in Essex — Colchester Old Town Stroll

Morning: Fly into London. From Stansted, take the Stansted Express to London Liverpool Street (~50 min), then Greater Anglia to Colchester (~50–55 min). Door-to-door in ~2–2.5 hours. Book trains on Omio. If you’d rather avoid central London, compare coaches too (~1.5–2 hours).

Afternoon: Check in and shake off the journey with a walk through Castle Park. Pop into Colchester Castle Museum for the story of Camulodunum, the Trinovantes, and Boudicca’s revolt. Coffee pick-me-up at Two Brews (silky flat whites, rotating roasters) or Crouch Street Bakes for gooey brownies.

Evening: Dinner at The Old Siege House—once caught in the English Civil War—now serving well-executed steaks, seafood, and seasonal veg. Nightcap at The Purple Dog or a local microbrew at Three Wise Monkeys.

Day 2: Roman Roots, Contemporary Art, and Castle Park Picnic

Morning: Walk a section of the Roman Wall and see the Balkerne Gate, Britain’s oldest surviving town gate. Swing by Firstsite for a smart mix of contemporary exhibitions and community art; the crescent-shaped building is a photo magnet.

Afternoon: Casual lunch at North Hill Noodle Bar (char siu ramen or pad Thai hit the spot). Then Castle Park for a riverside amble; rent a paddle boat in season or simply laze on the lawns. If wildlife is your thing, Colchester Zoo is one of the UK’s best for conservation-led exhibits.

Evening: Book Mercury Theatre (revivals, new writing, and touring shows). Dinner at Grain—think scallop crudo, heritage beets, and deft sauces—paired with a small but sharp wine list.

Day 3: Dedham Vale (Constable Country) Day Trip

Morning: Bus or taxi to Dedham (20–30 min). Follow the riverside path along the Stour toward Flatford Mill and Willy Lott’s House, landscapes immortalized by John Constable. Easy, flat walking; bring waterproofs if rain threatens.

Afternoon: Long lunch at The Sun Inn (Dedham): East Anglian produce, homemade pasta, local game in season. Alternatively, Milsoms (terrace dining and a brasserie vibe). Return via Constable’s walk or rent a rowboat in summer.

Evening: Back in Colchester, keep it cozy with tapas and a glass at Three Wise Monkeys’ rooftop (seasonal) or craft cocktails at Twisters Bar.

Chelmsford

Essex’s county town mixes a handsome cathedral, green parks, and the elegant Hylands Estate. It’s a perfect hub for Maldon’s maritime heritage, the tearooms at Heybridge Basin, and a day trip to the seaside at Southend-on-Sea and Leigh-on-Sea.

• Top sights: Chelmsford Cathedral, Central Park, Hylands House & Estate, Chelmer & Blackwater Navigation, and Bond Street riverside shopping.
• Eat & drink: Acanteen (brunch institution), Moto Pizza (fun, bottomless-by-the-slice concept), Galvin Green Man in Great Waltham (refined, pubby warmth), and Small Talk Tearooms (classic scones).
• Stay: Compare stays in Chelmsford on VRBO or browse hotels on Hotels.com. Stay near the Cathedral or Bond Street for easy dining.

Day 4: Transfer to Chelmsford, Maldon & Heybridge Basin

Morning: Train Colchester → Chelmsford (~20–25 min; ~$10–15) via Greater Anglia. Book on Omio. Drop bags and grab coffee at Acanteen (try the seasonal pancakes or a shakshuka).

Afternoon: Bus 31/31B to Maldon (~35–45 min). Stroll Promenade Park, watch Thames barges on the Blackwater estuary, then continue along the canal to Heybridge Basin. Order a cream tea at The Lock (a Tiptree-run tearoom famous for jam) and watch boats squeeze through the sea lock.

Evening: Back in Chelmsford for dinner at Moto Pizza (lively, great for groups) or book a taxi to Galvin Green Man in Great Waltham for an elevated seasonal menu—think native oysters, roast Suffolk chicken, and clever desserts.

Day 5: Southend-on-Sea & Leigh-on-Sea — Seaside Day Trip

Morning: Train Chelmsford → Southend Victoria (usually change at Shenfield; ~50–60 min; ~$15–20). Book via Omio. Walk the esplanade and head for Southend Pier—the world’s longest pleasure pier. Ride the little pier railway if you fancy the breeze without the 1.3-mile walk.

Afternoon: Lunch at The Pipe of Port (Southend) for steak pies and a serious wine list in a candlelit cellar, or go seaside-simple with fish and chips at The Frying Pan. Hop a short train or bus to Leigh-on-Sea Old Town to explore cobbled lanes, artists’ studios, and the cockle sheds.

Evening: Seafood feast: Osborne Bros at the sheds for cockles, prawns, and dressed crab with sea views, or The Peterboat for a pubby sit-down overlooking the creek. Gelato at Gelato Italiano, then return to Chelmsford.

Day 6: Hylands Estate, Paper Mill Lock, and the Chelmer & Blackwater

Morning: Hylands House & Estate: wander the elegant rooms (check opening hours) and roam landscaped grounds, woodlands, and ornamental gardens. Coffee and a pastry at The Stables café.

Afternoon: Taxi or bus to Paper Mill Lock (Little Baddow). Amble the towpath beside the still waters of the Chelmer & Blackwater Navigation; birdwatching is excellent. Light lunch or cream tea at Paper Mill Lock Tea Rooms, or pack a picnic and watch narrowboats glide past.

Evening: Back in Chelmsford. Casual dinner at Acanteen (solid veggie choices, Essex suppliers) or The New London (modern British; smart-casual) with a gin-and-tonic made from local distillers.

Day 7: Cathedral, Markets, and Departure

Morning: Quiet time in Chelmsford Cathedral—airy, light-filled, and welcoming. Browse Bond Street for last-minute local products (look for Maldon sea salt and Tiptree jams).

Afternoon: Depart for your flight. From Chelmsford, trains reach London Liverpool Street in ~30–35 minutes; Stansted is ~60–75 minutes with a change. Compare options on Omio and flights on Trip.com or Kiwi.com.

Evening: If you have extra time, toast the trip with a final pint at a riverside pub—or a last scone before you go.

Bonus Bites & Local Gems

• Mersea Island (from Colchester): For a future visit or if you swap a day, head to West Mersea for lunch at The Company Shed (no-frills, super-fresh seafood; arrive early) or The Oyster Bar; walk Cudmore Grove Country Park and check tide times for The Strood causeway.
• Hadleigh Castle: Ruined cliff-top fortress with sweeping Thames estuary views; pair with Leigh-on-Sea.
• Seasonal events: Southend’s seafront fireworks (select summer dates), Maldon’s barge regattas, and Christmas markets across Essex.

Where to Stay, Quick Links:
Colchester stays: VRBO | Hotels.com
Chelmsford stays: VRBO | Hotels.com
Southend-on-Sea stays (if you add a night): VRBO | Hotels.com

This 7-day Essex itinerary threads together Roman walls, manor houses, and a proper dose of sea air. You’ll taste the county—oysters, Maldon salt, Tiptree jam—while exploring landscapes that inspired a master painter. It’s an easy, rich escape within an hour of London, and one you’ll be tempted to repeat.