We are currently in that strange, timeless wormhole between Christmas Day and New Year’s Eve. You know the one: you aren’t quite sure what day of the week it is, wearing pyjamas at 2 PM is socially acceptable, and your main food group is cheese.
But there comes a moment when the fresh air calls. Whether you are a Stratford local needing to escape a house full of relatives, or a visitor looking to see the Bard’s town without the summer crowds, winter is actually one of the most magical times to explore Stratford-upon-Avon.
The Avon often sits high and moody, the frost clings to the thatch in Shottery, and—most importantly—the pubs have their fires roaring.
Here is our curated selection of the best walks to tackle this week, ranging from gentle paved strolls to muddy adventures, complete with our signature “Pit Stop Picks” for that essential post-walk refreshment.
🎒 The Winter Walker’s Checklist
Before you head out, make sure you are prepped for a Warwickshire winter:
- Footwear: If you are leaving the pavement (Walks 2 and 4), wellies or heavy hiking boots are non-negotiable. It has been a wet December!
- Layers: The wind chill off the Avon can be biting.
- Timing: Remember, the sun is setting around 4:00 PM. Don’t get caught on the Welcombe Hills in the dark!
1. The “Pavements & Pints” Classic: The Historic Riverside Loop
Difficulty: Easy (Paved & Flat) | Distance: Approx. 2 Miles
If you have the pushchair in tow, or you are wearing box-fresh trainers you don’t want to ruin, this is the walk for you. It’s the classic Stratford loop, but it takes on a different character in winter.
Start at the Tramway Bridge. Instead of heading straight into town, cross over to the Rec (Recreation Ground) side. The views across the water toward the RSC theatre are spectacular on a crisp grey day. Follow the path down past the bandstand and cross back over via the footbridge at Lucy’s Mill.
This brings you out near Holy Trinity Church. Walking back up through the churchyard (where Shakespeare rests) in the quiet of winter is incredibly atmospheric. Loop back via Southern Lane, passing the stage door of The Other Place and the Swan Theatre.
🍺 Pit Stop Pick: The Dirty Duck (Black Swan)
You simply cannot do this walk without stopping at The Dirty Duck on Waterside. It is the quintessential actor’s pub. In winter, the front bar is cosy, dimly lit, and usually filled with chatter about the latest panto or RSC production. Grab a pint of Purity and warm up.
Look out for: The distinct lack of rowboats. With the river traffic gone, the swans rule the Avon in December. See if you can spot the “Teenage” cygnets—they are losing their grey feathers and turning white right about now.
2. The “Blow Away the Cobwebs”: The Welcombe Hills & Obelisk
Difficulty: Moderate (Hilly & Muddy) | Distance: 2-3 Miles
Feeling guilty about that third helping of Christmas pudding? This is the antidote. The Welcombe Hills offer the best elevation in Stratford, located just to the north of the town centre.
Park at the Maidenhead Road car park (if you can find a space—it’s popular!) or walk up from the town. The terrain here is undulating tussocky grassland and woodland. Head straight for the Obelisk. Standing beneath this stone monument provides a panoramic view across the Avon Valley. On a clear winter day, you can see for miles; on a foggy day, it feels like something out of a Gothic novel.
Be warned: The “dingles” (the steep valleys in the hills) are notorious mud-traps this time of year. If you slide down, you are staying down until spring!
📸 The “Golden Hour” Challenge
Engagement Alert: The Welcombe Hills face west-ish. If you can time your walk for 3:15 PM, you might catch the low winter sun hitting the spire of Holy Trinity Church in the distance. Snap a photo and tag us @WhatsUpStratford—we’ll share the best “Winter Skylines” this week!
3. The Family Adventure: The Stratford Greenway to Milcote
Difficulty: Easy (Flat & Surfaced) | Distance: 5 Miles (There and back)
Did the kids get new bikes or scooters from Santa? The Stratford Greenway is your best friend. This converted railway line runs from Seven Meadows Road out to Long Marston, but walking to Milcote and back is usually enough for little legs.
Because it is an old railway line, it is dead straight and dead flat. It’s also lined with trees, which provides a surprising amount of shelter if the wind is howling. It’s a great social walk—wide enough for groups to walk three or four abreast without being mowed down by traffic.
☕ Pit Stop Pick: Bobby’s at Milcote
Halfway along (at the Milcote car park), you will find Bobby’s, a café housed in a converted 1950s railway carriage. There is something delightfully nostalgic about drinking a hot chocolate with whipped cream inside an old train carriage while the windows steam up. Check their social pages for holiday opening hours!
4. The Romantic Ramble: Town to Shottery
Difficulty: Easy/Moderate (Paved & Field Paths) | Distance: 2.5 Miles
Stratford isn’t just about the river. A walk out to the village of Shottery feels like stepping back in time. Start in the town centre and head towards the college, picking up the footpath that cuts across the fields (Shottery Fields).
The stark, bare trees in winter frame Anne Hathaway’s Cottage beautifully. Without the leaves, you can see the structure of the timber framing much more clearly. The gardens are dormant, but the structure of the willow arbours and the smoke curling from the chimneys of the surrounding thatched cottages creates a perfect winter scene.
Interactive Idea: Play “Thatch Bingo.” Count how many thatched roofs you spot between the college and the cottage. Loser buys the drinks at the end.
🍷 Pit Stop Pick: The Bell Inn
Conveniently located just around the corner from the Cottage, The Bell is a proper hearty pub. It’s dog-friendly, usually has a roaring fire, and serves a mean Sunday Roast if you are walking on the weekend.
❄️ The Stratford Winter Scavenger Hunt
Dragging teenagers or bored children along? Give them this list to check off to keep the complaining to a minimum:
- ✅ A Narrowboat with smoke coming out the chimney (Bonus points if you smell coal).
- ✅ A “Garrick” Lamppost (The black vintage ones in town).
- ✅ A Robin (They love the hedgerows along the Greenway).
- ✅ A RSC Poster advertising a play you haven’t seen yet.
- ✅ A Dog in a Christmas Jumper (Almost guaranteed on the Rec).
Final Thoughts
However you choose to spend these last few days of the year, getting outside is the best way to reset before January kicks in. Stratford-upon-Avon is beautiful in the bloom of summer, but it is soulful in the winter.
Happy Walking!
