Best points of interest near Chester
26 points of interest · 26 ranked · updated 2026-07-15 · off-season
Explore the best points of interest near Chester, Vermont — every spot ranked by our conditions-aware Snoflo score: live conditions first, then visitor reviews and logged trips. Click a pin on the map for the score and what's driving it.
Showing the top 15 of 26 points of interest · best 15 shown on the map
J⛰
#1
Jeffrey House
2.2 mi away
The Jeffrey House is a historic house on North Street in Chester, Vermont United States. Built in 1797, it is one of Vermont's small number of surviving Georgian style houses. It…
Why 40: protected / landmark status
40Rated
A⛰
#2
Augustus and Laura Blaisdell House
2.6 mi away
The Augustus and Laura Blaisdell House is a historic house at 517 Depot Street in Chester, Vermont. Built in 1868 for a local businessman, it is a fine local example of…
Why 40: protected / landmark status
40Rated
F⛰
#3
Fire District No. 2 Firehouse
2.6 mi away
The Fire District No. 2 Firehouse, also known locally as the Yosemite Engine House, is a historic fire station at 716 Depot Street in Chester, Vermont, United States. Built in…
Why 40: protected / landmark status
40Rated
G⛰
#4
Green Mountain Railroad
2.6 mi away
Green Mountain Railroad is a heritage railroad attraction located in Vermont near Keene. The railroad offers scenic train rides through the region's countryside. Visitors can…
Why 40: protected / landmark status
40Rated
G⛰
#5
Gingerbread Apartments
3.0 mi away
The Greenwood House, now the Gingerbread Apartments, is a historic house on Vermont Route 103 in Chester, Vermont. Built about 1850 and restyled about 1900, it is an…
Why 40: protected / landmark status
40Rated
P⛰
#6
Porter Turret Observatory
6.1 mi away
The Stellafane Observatory is an astronomical observatory in Springfield, Vermont, founded in 1920 by Russell W. Porter. The Pink Clubhouse was built in 1923 at the site by the…
Why 40: protected / landmark status
40Rated
B⛰
#7
Bartonsville Covered Bridge
6.4 mi away
The Bartonsville Covered Bridge is a wooden covered bridge in the village of Bartonsville, in Rockingham, Vermont, United States. The bridge is a lattice truss style with a…
Why 40: protected / landmark status
40Rated
L⛰
#8
Lockwood-Boynton House
6.9 mi away
The Lockwood-Boynton House is a historic site located near Rutland in central Vermont. Visitors to this preserved structure can explore an important example of the region's…
Why 40: protected / landmark status
40Rated
S⛰
#9
Springfield Art and Historical Society Museum
7.0 mi away
The Springfield Art and Historical Society Museum in Springfield, Vermont preserves local art and history. Located at an elevation of 485 feet near Rutland, the museum offers…
Why 40: protected / landmark status
40Rated
W⛰
#10
Williams Road
7.0 mi away
Williams Road is a bridge located near Keene in southwestern New Hampshire. Situated at coordinates 43.212°N, 72.536°W, this crossing provides access across the local landscape…
Why 40: protected / landmark status
40Rated
M⛰
#11
Mill Street
7.3 mi away
Mill Street is a bridge located near Rutland in central Vermont. Situated in a region characterized by natural landscapes and rural communities, the structure serves as a…
Why 40: protected / landmark status
40Rated
P⛰
#12
Pollard Block
7.3 mi away
The Pollard Block is a historic commercial building at 7 Depot Street in Cavendish, Vermont. Built in 1895, it is a fine local example of commercial Italianate architecture, and…
Why 40: protected / landmark status
40Rated
S⛰
#13
Spaulding Bridge
7.3 mi away
Spaulding Bridge is a bridge located near Rutland in central Vermont. The structure spans across the area at coordinates 43.381°N, 72.609°W, providing local crossing access in…
Why 40: protected / landmark status
40Rated
Points of Interest near Chester
The Chester area has 26 points of interest on Snoflo, ranked by live conditions, visitor reviews, and logged trips — so the best, closest options rise to the top.
How we rank the best points of interest near Chester
How are these points of interest ranked?
Each gets a daily Snoflo score blending live conditions, visitor review ratings, and logged trips. The order reflects what's best right now and re-ranks every day.
How often does it update?
Daily, as new conditions, reviews, and trips arrive — so "best right now" means right now.
What do the numbers on the map mean?
Each pin shows that spot's current Snoflo score; tap it for the breakdown and a link to the full report.