Introduction
If you’re anything like me—someone who enjoys discovering a place that blends history, nature, and a little small‑town charm—you’ll find Simsbury, Connecticut, to be a delightful weekend escape. I recently spent a couple of days wandering around this New England town nestled in the Farmington Valley, and what stood out was its rich mix of outdoor adventures, historic structures, farm visits, great food, and an un‑rushed pace. Here are the 12 best & fun things to do in Simsbury, CT, drawn from my personal journey, with tips, photo‑moments, and local flavor.
12 Best & Fun Things To Do In Simsbury, CT (2026)
1. Hike Up to Heublein Tower at Talcott Mountain State Park
One of my most memorable outings was hiking up to Heublein Tower—perched atop Talcott Mountain and offering panoramic views over the valley. According to local visitor guides, the 165‑foot tower built circa 1911‑14 is now open to the public, and the trail to it provides a real “New England escape” feeling.
Tip: Go early in the morning when the air is crisp and the light is soft. Wear comfortable shoes, bring water, and be ready for the final climb to the tower. Don’t forget a camera—the view is worth it.
See Also: 19 Best & Fun Things To Do in Roscoe, NY
2. Walk the Historic Town Center
On arriving in Simsbury, I strolled through the town center along Hopmeadow Street, admiring the historic architecture, small cafés, and shops. One notable landmark is the Eno Memorial Hall—a classical‑revival building built in 1932, listed on the National Register. This area gives you a feel of “classic New England town meets modern life.”
Tip: Grab coffee, browse a local bookshop or gallery, and take your time—this is a place to slow down.
3. Cross the Charming Drake Hill Road Bridge (“Flower Bridge”)
I loved discovering the Drake Hill Road Bridge—an 1892 Parker truss bridge over the Farmington River, now a pedestrian landmark adorned with seasonal flower boxes. It’s relaxed, photo‑friendly, and deeply local.
Tip: Visit in either late spring/summer when the flowers are in full bloom or in autumn for rich foliage reflections in the river.
4. Visit Farms & Ice Cream at Tulmeadow Farm Store
One of the lighter and fun stops: I visited Tulmeadow Farm Store — a dairy farm in operation since 1768, offering fresh produce, dairy and what many claim is “the world’s best ice cream”.
Tip: Gust for their seasonal flavours, pick up fresh produce and plan a picnic with goodies from the farm.
5. Explore Nature at Belden Forest
For a quieter nature moment, I headed to Belden Forest — a 40‑acre old‑growth woodland featuring tall eastern white pines and other native trees, permanently protected. It’s a peaceful trail and nature fix.
Tip: Bring a map or use a trail app because signage is minimal. Go slowly, listen to the forest — you’ll feel far away from town even if you’re minutes away.
6. Check Out the Historic Pinchot Sycamore & Farmington River
Simsbury hides some gems: the Pinchot Sycamore is the largest tree in Connecticut — a massive sycamore over 200 years old, located by the Farmington River. I found this a great stop for quiet reflection and easy nature access.
Tip: Bring a blanket and snack. After visiting the tree, take a walk along the riverbank and enjoy the gentle flow and shade.
7. Enjoy the Outdoors at Stratton Brook State Park
For families or those wanting a gentler hike, Stratton Brook State Park offers woodlands, trails, a pond and a historic pavilion built by the CCC. It’s a great all‑rounder.
Tip: Summer = picnic, paddle or gentle trail. Winter = cross‑country ski or snowshoe if conditions allow.
8. Visit the Farm Trail & Seasonal Harvest at Farms
Simsbury’s farming tradition is very much alive. For example, you can visit Rosedale Farms & Vineyard or Flamig Farm to experience CSA, hayrides, pumpkins in fall, and fresh produce.
Tip: In autumn, plan for pumpkins and hayrides. In summer, check farmer’s markets or open‑farm days. It’s an especially good stop if you’re travelling with children.
9. Attend a Concert or Event at Simsbury Meadows Performing Arts Center
For a bit of cultural flair, Simsbury Meadows hosts summer music concerts and events. The visitor guide mentions that the Hartford Symphony Orchestra and other acts perform there.
Tip: Check the event calendar ahead of time. Bring a blanket or lawn chair, arrive early for parking and enjoy an evening outdoors with music.
10. Explore Historic Houses & Museums
For those who appreciate historic architecture and stories, the Phelps Tavern Museum and the local Historical Society offer tours of colonial‑era homes and interpretive exhibits.
Tip: Take a guided tour if you can—it deepens the experience. Afterwards, pop into a historic café or house museum gift shop for a unique souvenir.
11. Relish Local Food, Cafés & Shops
What I enjoyed most between excursions were the cafés, farm‑to‑table restaurants, and independent shops scattered around Simsbury. While not always flashy, the local flavor is strong and genuine.
Tip: Try a brunch café downtown, pick up a local bakery treat, and support a boutique craft shop. In the evening, consider a cozy local restaurant rather than a big chain.
12. Drive or Bike the Farmington River Trail & Scenic Backroads
Finally, if you want a more relaxed outdoor end to your day, take the Farmington River Trail or drive some of the scenic backroads of the Farmington Valley. Locals mention tubing the river, cycling the trail or simply driving for foliage.
Tip: Bring your bike or rent one. Plan a sunset ride or drive. Stop at a scenic overlook, bring a light snack, and just enjoy the valley’s pace.
Final Thoughts
Visiting Simsbury, CT, felt like discovering a place that offers both unexpected adventures and comfort of familiarity. I took in trails and views and historic rooms and farms—and what tied them all together was a sense of genuine place.
Here are a few take‑aways from my trip:
- Balance your pace. I mixed hikes and quiet woods with relaxed food stops and historic house walks. That made the trip rich but not exhausting.
- Enjoy the local rhythm. It wasn’t about ticking off big tourist attractions—it was about being present: sipping coffee, looking out over the river, walking a trail at dusk.
- Pack smart. Depending on the season: layering for hikes; camera for scenic spots; comfortable shoes; bug spray for woodland paths; and a sense of exploration.
- Look for seasons. In fall the foliage became part of the experience; in summer the farms and ice‑cream added flavour. Simsbury changes beautifully through the year.
- Support small places. The local farms, cafés, and historic tours—these made the place feel personal and real.