Winter Breaks in Stamford: Where to Stay, Eat & Wander

Winter is a great time to visit Stamford. The town is compact, easy to explore on foot and full of places that feel especially welcoming at this time of year. As people who live and work here - and who host guests throughout the season - we know what makes a winter weekend work well: a comfortable place to stay, good food close by, and enough to do without needing a packed itinerary. Here’s how we recommend spending a winter break in Stamford.

Where to Stay - no surprises for guessing our recommendations here!

The William Cecil

Just on the edge of the town centre, at The William Cecil we can give you a relaxed hotel stay with Stamford within easy walking distance. Rooms are comfortable and well considered, and with our own direct entrance onto The Burghley Estate makes it the perfect base if you like to head out for a walk before or after breakfast. In winter, it’s particularly appealing for guests who want a quieter setting with excellent dining and a sense of space, without feeling removed from the town.

The Bull & Swan

If you’d prefer a cosy pub stay, The Bull & Swan puts you exactly where you want to be. Our rooms make winter weekends refreshingly simple - check in, enjoy dinner and drinks in the pub, then in the morning, you’re walking distance to town, with shops, cafés and riverside walks all close at hand.

Both are ideal bases for a winter stay - the choice is yours.

Where We Eat & Drink

Food and drink are central to any stay, and Stamford has a strong mix of relaxed and refined options if you decide to venture further than our two fabulous spots.

Milly’s Bistro.

At Milly’s, our seasonal menus focus on quality ingredients and confident cooking, served in a welcoming, unfussy setting. It works equally well for a long lunch or an evening meal......

The Bull & Swan

In winter, the pub really comes into its own. Expect well-kept pints, generous food and a lively but comfortable atmosphere. It’s an easy choice after a walk or for an evening you don’t want to over-plan.

Other Stamford spots we recommend a visit:

• Paten & Co for cocktails and an energetic evening atmosphere

• The Wine Bar for a relaxed glass of wine and small plates

• The George of Stamford for a more traditional setting with a sense of occasion

• The Tobie Norris for pizza, pints and a classic Stamford pub atmosphere

• Pizza Da Mario for authentic Neapolitan pizzas

• The Blonde Beet for daytime coffee and plant-based dishes

All are within easy reach and suit the kind of flexible days winter weekends tend to bring.

Where We Wander in Winter

One of the things our guests often comment on is how easy Stamford is to explore on foot. Winter walks here don’t need to be ambitious - just well chosen - and there’s a good mix of riverside paths, open parkland and historic streets that work well at this time of year.

The River Welland & Stamford Meadows

A walk along the River Welland and across the Meadows is one of the simplest ways to step out of town without going far. The paths are clear throughout winter and offer a straightforward route for a short walk before lunch or a longer loop if you have time. From both The William Cecil and The Bull & Swan, it’s easy to reach on foot, making it a natural part of a winter stay rather than a planned excursion.

Burghley Park

Burghley Park sits just outside Stamford and is well worth including in a winter weekend. While the house and formal gardens close during the winter months, the deer park remains open for walking all year. The landscape is open and spacious, with well-maintained paths that suit winter conditions, and it’s ideal if you’re looking for a longer walk before returning to town. We often recommend hiring one of our Pashley bikes to take in the views.

Historic Streets & Independent Shops

Back in town, walking is as much about exploring as it is about getting from one place to another. Stamford’s historic centre is compact and well preserved, with stone buildings, small lanes and a strong collection of independent shops. We usually point guests towards St Paul’s Street, Broad Street, High Street and the surrounding lanes, where you can browse at your own pace, stop for coffee and dip in and out of shops without covering much ground.

Photo courtesy of The Old Building

Cafés, Galleries & Warm Stops Along the Way

One of the advantages of wandering in Stamford is how easy it is to break up a walk with a warm stop. Cafés, pubs and small galleries are scattered through the centre, so you can head out, explore for an hour or two, then settle somewhere comfortable before moving on again. It’s a flexible way to spend a winter afternoon and suits shorter days and colder weather.

Photo courtesy of The Old Building

Together, these walks give you a good sense of Stamford without overplanning. Whether you’re heading out for fresh air before breakfast, taking a longer walk through Burghley Park, or simply wandering the streets between meals, winter days here are easy to shape around what feels right at the time.