10 Things to Do in Brookfield That You Shouldn't Miss

November 3, 2017 Jacquiline Delozier

Brookfield is an affluent town in Fairfield County, Connecticut, United States, situated within the southern foothills of the Berkshire Mountains. The population was 16,487 at the 2010 census. The town is located 43 miles (69 km) northeast of New York City, making it part of the New York metropolitan area. Brookfield was first settled in 1710 by John Muirwood, as well as other colonial founders including Hawley, Peck and Merwin. They bartered for the land from the Wyantenuck Nation and the Pootatuck nation who were ruled under the Sachem Waramaug and Pocono. The purchase of the southern portion of town involved the current municipal center where sachem Pocono then had his village and lived in an enormous palisade along the Still River. Eventually, when the town was settled, it was first established as the Parish of Newbury, which incorporated parts of neighboring Newtown and Danbury. The town of Brookfield was established in 1788. It was named after the first minister of the parish's Congregational church, Reverend Thomas Brooks.
Restaurants in Brookfield

1. Tarrywile Park & Mansion

70 Southern Blvd, Danbury, CT 06810-7943 +1 203-744-3130
Excellent
67%
Good
29%
Satisfactory
3%
Poor
0%
Terrible
1%
Overall Ratings

4.5 based on 154 reviews

Tarrywile Park & Mansion

Reviewed By Reactor1966 - Danbury, Connecticut

I rented the mansion for my wife's Roaring 20's birthday party, and it could not have been a more perfect setting for the party. You don't even need to decorate the place, it has so much character. Like something out of a movie. It's no wonder so many people get their pictures taken here.

2. Squantz Pond State Park

Route 39, New Fairfield, CT +1 860-424-3200
Excellent
34%
Good
48%
Satisfactory
12%
Poor
6%
Terrible
0%
Overall Ratings

4 based on 47 reviews

Squantz Pond State Park

Reviewed By Samantha N

Squantz Pond is certainly quieter than Candlewood Lake (right across the way) but it a great place to spend the day or just afternoon! For a beginner kayaker - this lake is perfect to work on your skills or just float around looking at all the different houses. Remember that after Memorial Day you have to pay to park, especially at the boat launch and spots fill up fast!

3. Blue Jay Orchards

125 Plumtrees Rd, Bethel, CT 06801-3102 +1 203-748-0119
Excellent
59%
Good
34%
Satisfactory
5%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 72 reviews

Blue Jay Orchards

Reviewed By Bernardo F - New York City, New York

A nice countryside farm and gift store. Lots of different treats for sale, and it's a fine place to spend some time on an afternoon.

4. Lovers Leap State Park

Grove Street, New Milford, CT 06776
Excellent
54%
Good
44%
Satisfactory
0%
Poor
2%
Terrible
0%
Overall Ratings

4.5 based on 49 reviews

Lovers Leap State Park

Reviewed By Bernardo F - New York City, New York

It was a very nice natural forested park. We were attracted first by the beautiful old iron bridge over the river, and there were other information signs too telling about the history of the owners of the area and previous homes on the land. Nice park.

5. Edmond Town Hall Theater

45 Main St, Just Past the Flag Pole, Newtown, CT 06470-2134 +1 203-426-2475
Excellent
78%
Good
22%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 44 reviews

Edmond Town Hall Theater

Reviewed By Jeffrey T - connecticut

Great place to see a movie for a few dollars--free on the third Saturday night of the month (thanks Ingersol Motors!). Concessions are inexpensive and while you are there get lost in the building whether it be looking at the amazing paintings on the walls of the stairways or looking at the old gym filled with memories, or just poking around. Great building and the center of Newtown. When you go outside, look at the benches and what's written as well as checking out the plaque by the mailboxes.

6. Promisek's Historic Garden

694 Skyline Ridge Rd, Three Rivers Fam, Bridgewater, CT 06752-1734 +1 860-350-8226
Excellent
0%
Good
100%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

4 based on 1 reviews

Promisek's Historic Garden

Reviewed By Nancy K - Southbury, Connecticut

A formal stonewalled garden designed by Beatrix Farrand in 1921, this garden was brought back to life in 1992. The stone walkways make browsing through the garden, a beautiful mixture of perennials and annuals, very easy. Be sure to go through the gate in the back to see the teardrop shaped pool, amphitheater, and pergola that were once used in the 1930s. Although officially only open on the last Sunday in June (CT Garden Day), this garden welcomes visitors who call ahead and make an appointment for a tour.

7. Bridgewater Chocolate Factory and Factory Store

559 Federal Rd, Brookfield, CT 06804-2017 +1 203-775-2286
Excellent
68%
Good
22%
Satisfactory
4%
Poor
6%
Terrible
0%
Overall Ratings

4.5 based on 44 reviews

Bridgewater Chocolate Factory and Factory Store

Reviewed By saltcreekct - Danbury, Connecticut

Always nice to have a local chocolate maker. They offer pre-made boxes or you can select and customize. Variety is good and quality is good too, though not as artisan as other places we have visited. Still, friendly help and a solid -- if pricey -- chocolate shop.

8. DiGrazia Winery

131 Tower Rd, Brookfield, CT 06804-3654 +1 203-775-1616
Excellent
60%
Good
27%
Satisfactory
7%
Poor
3%
Terrible
3%
Overall Ratings

4.5 based on 54 reviews

DiGrazia Winery

Reviewed By Neg156 - Litchfield, Connecticut

Visited this winery on Mother's Day. Winery is at the residence of the owners Dr. DiGrazia and his wife. Sat outside under the pergola next to the babbling fountain nearby, but there were other tables outside on the lawn too. Dr. DiGrazia poured our tasting. He was a wealth of information about the wine process, his life and the people he has met. I could have spent the whole day talking to him. Loved All of wines we tasted but my favorites were Anastasia's blush and Sweet Magnolia. I highly recommend this winery.

9. Elephant's Trunk Flea Market

490 Danbury Road, Danbury, CT +1 860-355-1448
Excellent
53%
Good
30%
Satisfactory
14%
Poor
2%
Terrible
1%
Overall Ratings

4 based on 172 reviews

Elephant's Trunk Flea Market

Reviewed By RamonaL34

The Elephant’s Trunk Flea Market is one of the best flea markets I have ever been to. There is everything you can imagine there, plants, furniture, homemade items, collector cards (baseball, football, etc), toys, coins, jewelry, clothing, pictures, books, buttons, sewing machines, vintage everything, it is amazing! You can really find some unique items. I found a 1940s Blue Jacket Manual for $10.

There are food vendors on site too in case you get hungry. All are food trucks with some wonderful smells coming out of them.

The only drawback to me was the porta potties. Just go before you get there if you are like me and prefer not to use them. I will say that the ones on the far end from the entrance were surprisingly clean.

Parking is easy and free.

Do not miss the Elephant’s Truck Flea Market if you enjoy flea markets, you will not be disappointed.

10. Harrybrooke Park

100 Still River Dr, New Milford, CT 06776
Excellent
72%
Good
23%
Satisfactory
5%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 34 reviews

Harrybrooke Park

Reviewed By Howard R - New Milford, Connecticut

This is a large, well maintained, town park. The center is largely open and there are some trees and a small river boarding the edges. A walk around the periphery takes about 30 minutes. I know It is used for scouting events and town BBQs. Not exciting, but pleasant enough if you want to get out of the house on a nice day.

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